e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Synthesis of a marine polyether toxin, okadaic acid [4] p1--total synthesis

M Isobe, Y Ichikawa, DL Bai, H Masaki, T Goto

Index: Isobe, Minoru; Ichikawa, Yoshiyasu; Bai, Dong-Lu; Masaki, Hisanori; Goto, Toshio Tetrahedron, 1987 , vol. 43, # 20 p. 4767 - 4776

Full Text: HTML

Citation Number: 97

Abstract

Three segments A, B and C for okadaic acid synthesis were coupled with each other in the order of A+ (B+ C), the key steps of the twice couplings being between sulfone carbanions and aldehydes. After the B+ C coupling, the asymmetric center C-27 was generated by a hydride reduction of the corresponding ketone 16 under electronic control. The second coupling was followed to form the C-14 15 double bond. Oxidation of the α-oxy aldehyde ...

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

Structure

~64%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

Structure

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

(2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-carbaldehyde Structure

(2R,4a'R,5R,6'S...

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

(2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-carbaldehyde Structure

(2R,4a'R,5R,6'S...

Structure

~%

(2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-carbaldehyde Structure

(2R,4a'R,5R,6'S...

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

(2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-carbaldehyde Structure

(2R,4a'R,5R,6'S...

Structure

~%

(2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-carbaldehyde Structure

(2R,4a'R,5R,6'S...

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methanol Structure

((2R,4a'R,5R,6'...

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methanol Structure

((2R,4a'R,5R,6'...

Structure

~%

((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methanol Structure

((2R,4a'R,5R,6'...

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methanol Structure

((2R,4a'R,5R,6'...

Structure

~%

((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methanol Structure

((2R,4a'R,5R,6'...

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

Structure

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

Structure

Structure

~%

Structure

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

(((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

(((2R,4a'R,5R,6...

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

(((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

(((2R,4a'R,5R,6...

Structure

~%

(((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

(((2R,4a'R,5R,6...

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

(((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

(((2R,4a'R,5R,6...

Structure

~%

(((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

(((2R,4a'R,5R,6...

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

(S)-1-((2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-one Structure

(S)-1-((2R,4a'R...

~%

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

Structure

~%

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

~%

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

Structure

~%

(2R,4a'R,5R,6'S,8'R,8a'S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6'-((1S,3S)-1-hydroxy-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-8'-ol Structure

(2R,4a'R,5R,6'S...

(2R,4a'R,5R,6'S,7'S,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-carbaldehyde Structure

(2R,4a'R,5R,6'S...

~%

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

Structure

~%

(1S,3S)-1-((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-8'-(methoxymethoxy)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-6'-yl)-3-((2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol Structure

(1S,3S)-1-((2R,...

Synthetic studies toward marine toxic polyethers [5] the tot...

[Isobe, Minoru; Ichikawa, Yoshiyasu; Goto, Toshio Tetrahedron Letters, 1986 , vol. 27, # 8 p. 963 - 966]

Synthetic studies toward marine toxic polyethers [5] the tot...

[Isobe, Minoru; Ichikawa, Yoshiyasu; Goto, Toshio Tetrahedron Letters, 1986 , vol. 27, # 8 p. 963 - 966]

Synthetic studies toward marine toxic polyethers [5] the tot...

[Isobe, Minoru; Ichikawa, Yoshiyasu; Goto, Toshio Tetrahedron Letters, 1986 , vol. 27, # 8 p. 963 - 966]