Tetrahedron letters

Synthetic studies toward marine toxic polyethers [5] the total synthesis of okadaic acid

M Isobe, Y Ichikawa, T Goto

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

Full Text: HTML

Citation Number: 84

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... The total synthesis of okadaic acid has been accomplished through the coupling of all the segments, A, B and C, by means ofsulfone-carbanion strategy. ... For stereochemistry of the alcohol 11, see Ref #2b; 1 H nmr of 11 δ 0.88(3H d J=6), 1.03(3H d J=6), 1.04(9H s), ...

 Related Synthetic Route
(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

Structure

104307-03-1

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

Structure

104307-03-1

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

104306-99-2

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

~%

Structure

104307-03-1

((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)methanol Structure

109413-94-7

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

~%

Structure

104307-03-1

(((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-8'-(methoxymethoxy)-6'-((trityloxy)methyl)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

104307-00-8

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

~%

Structure

104307-03-1

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

(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

104307-04-2

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

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

(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

104307-04-2

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

Structure

104307-03-1

~%

(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

104307-04-2

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

(((2R,4a'R,5R,6'R,7'R,8'R,8a'R)-7'-(benzyloxy)-8'-(methoxymethoxy)-6'-((trityloxy)methyl)octahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)methoxy)(tert-butyl)diphenylsilane Structure

104307-00-8

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

~98%

((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)methanol Structure

109413-94-7

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

Structure

115352-19-7

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

Structure

115352-19-7

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

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

104306-99-2

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

Structure

104307-12-2

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

Structure

104307-12-2

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

Structure

104307-11-1

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

Structure

104307-11-1

((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

104307-08-6

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

~83%

(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

104307-09-7

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

(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

104307-09-7

(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

104307-07-5

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

~95%

((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

104307-08-6

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

(((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

104307-07-5

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

(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

104307-06-4

(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

104307-04-2

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

~60%

(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

104307-05-3

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

(R)-1-((2R,3R,4R,5R,6R)-3-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-hydroxyheptan-3-one Structure

115369-32-9

(R)-1-((2R,3R,4...

~%

(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

104307-05-3

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

(6R)-1-((4aR,6R,7R,8S,8aR)-7-(benzyloxy)-8-(methoxymethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)-7-((tert-butyldiphenylsilyl)oxy)-6-(1-ethoxyethoxy)heptan-3-one Structure

104306-97-0

(6R)-1-((4aR,6R...

~%

(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

104307-05-3

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


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