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

Synthesis and absolute stereochemistry of roseophilin

PE Harrington, MA Tius

Index: Stetter, Hermann; Haese, Wilfried Chemische Berichte, 1984 , vol. 117, # 2 p. 682 - 693

Full Text: HTML

Citation Number: 120

Abstract

... Volume: Page ... The transformation was accomplished very conveniently through the Stetter reaction of 18 with 6-heptenal 19 ... 22R,23R)-roseophilin in 15 steps and in 7.0% overall yield from 5-hexenal 13, taking into consideration the loss during crystallization of 2.

2-methylidene-2,3-dihydro-1H-inden-1-one Structure

2-methylidene-2...

Butyraldehyde Structure

~75%

2-(2-oxopentyl)-2,3-dihydroinden-1-one Structure

2-(2-oxopentyl)...

2-[(dimethylamino)methyl]-2,3-dihydroinden-1-one Structure

2-[(dimethylami...

~%

2-(2-oxopentyl)-2,3-dihydroinden-1-one Structure

2-(2-oxopentyl)...

Spiro(bicyclo(2.2.1)hept-5-en-2,2'-indan)-1'-on Structure

Spiro(bicyclo(2...

~%

2-(2-oxopentyl)-2,3-dihydroinden-1-one Structure

2-(2-oxopentyl)...

Spiro(bicyclo(2.2.1)hept-5-en-2,1'-cycloheptan)-2'-on Structure

Spiro(bicyclo(2...

~77%

2-methylidenecycloheptan-1-one Structure

2-methylidenecy...

N/A Structure

~%

2-methylidenecycloheptan-1-one Structure

2-methylidenecy...

Benzaldehyde Structure

2-Methylenecyclopentanone Structure

2-Methylenecycl...

~44%

2-phenacylcyclopentan-1-one Structure

2-phenacylcyclo...

3',4'-Dihydrospiro[bicyclo[2.2.1]hept-5-en-2,2'(1'H)-naphthalin]-1'-on Structure

3',4'-Dihydrosp...

~94%

2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE Structure

2-METHYLENE-1-O...

Propionaldehyde Structure

Propionaldehyde

2-Methylenecyclopentanone Structure

2-Methylenecycl...

~66%

2-(2-oxobutyl)cyclopentan-1-one Structure

2-(2-oxobutyl)c...

3',4'-Dimethylspiro(bicyclo(2.2.1)hept-5-en-2,1'-(3)cyclopenten)-2'-on Structure

3',4'-Dimethyls...

~87%

2,3-Dimethyl-5-methylene-2-cyclopenten-1-one Structure

2,3-Dimethyl-5-...

2-methylidene-2,3-dihydro-1H-inden-1-one Structure

2-methylidene-2...

Benzaldehyde Structure

~50%

2-phenacyl-2,3-dihydroinden-1-one Structure

2-phenacyl-2,3-...

2-[(dimethylamino)methyl]-2,3-dihydroinden-1-one Structure

2-[(dimethylami...

~%

2-phenacyl-2,3-dihydroinden-1-one Structure

2-phenacyl-2,3-...

Spiro(bicyclo(2.2.1)hept-5-en-2,2'-indan)-1'-on Structure

Spiro(bicyclo(2...

~%

2-phenacyl-2,3-dihydroinden-1-one Structure

2-phenacyl-2,3-...

Butyraldehyde Structure

2-Methylenecyclopentanone Structure

2-Methylenecycl...

~63%

2-(2-oxopentyl)cyclopentan-1-one Structure

2-(2-oxopentyl)...

2-Thiophenecarboxaldehyde Structure

2-Thiophenecarb...

2-Methylenecyclopentanone Structure

2-Methylenecycl...

~59%

2-(2-oxo-2-thiophen-2-ylethyl)cyclopentan-1-one Structure

2-(2-oxo-2-thio...

2-methylidenecycloheptan-1-one Structure

2-methylidenecy...

Butyraldehyde Structure

~32%

2-(2-oxopentyl)cycloheptan-1-one Structure

2-(2-oxopentyl)...

N/A Structure

~%

2-(2-oxopentyl)cycloheptan-1-one Structure

2-(2-oxopentyl)...

Spiro(bicyclo(2.2.1)hept-5-en-2,1'-cycloheptan)-2'-on Structure

Spiro(bicyclo(2...

~%

2-(2-oxopentyl)cycloheptan-1-one Structure

2-(2-oxopentyl)...

2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE Structure

2-METHYLENE-1-O...

Propionaldehyde Structure

Propionaldehyde

~63%

2-(2-oxobutyl)-3,4-dihydro-2H-naphthalen-1-one Structure

2-(2-oxobutyl)-...

3',4'-Dihydrospiro[bicyclo[2.2.1]hept-5-en-2,2'(1'H)-naphthalin]-1'-on Structure

3',4'-Dihydrosp...

~%

2-(2-oxobutyl)-3,4-dihydro-2H-naphthalen-1-one Structure

2-(2-oxobutyl)-...

2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE Structure

2-METHYLENE-1-O...

Hexanal Structure

~83%

2-(2-oxoheptyl)-3,4-dihydro-2H-naphthalen-1-one Structure

2-(2-oxoheptyl)...

3',4'-Dihydrospiro[bicyclo[2.2.1]hept-5-en-2,2'(1'H)-naphthalin]-1'-on Structure

3',4'-Dihydrosp...

~%

2-(2-oxoheptyl)-3,4-dihydro-2H-naphthalen-1-one Structure

2-(2-oxoheptyl)...

2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE Structure

2-METHYLENE-1-O...

Benzaldehyde Structure

~67%

2-phenacyl-3,4-dihydro-2H-naphthalen-1-one Structure

2-phenacyl-3,4-...

3',4'-Dihydrospiro[bicyclo[2.2.1]hept-5-en-2,2'(1'H)-naphthalin]-1'-on Structure

3',4'-Dihydrosp...

~%

2-phenacyl-3,4-dihydro-2H-naphthalen-1-one Structure

2-phenacyl-3,4-...

2-methylidenecycloheptan-1-one Structure

2-methylidenecy...

Valeraldehyde Structure

~51%

2-(2-oxohexyl)cycloheptan-1-one Structure

2-(2-oxohexyl)c...

N/A Structure

~%

2-(2-oxohexyl)cycloheptan-1-one Structure

2-(2-oxohexyl)c...

Spiro(bicyclo(2.2.1)hept-5-en-2,1'-cycloheptan)-2'-on Structure

Spiro(bicyclo(2...

~%

2-(2-oxohexyl)cycloheptan-1-one Structure

2-(2-oxohexyl)c...

Furfural Structure

2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE Structure

2-METHYLENE-1-O...

~62%

2-[2-(furan-2-yl)-2-oxoethyl]-3,4-dihydro-2H-naphthalen-1-one Structure

2-[2-(furan-2-y...

3',4'-Dihydrospiro[bicyclo[2.2.1]hept-5-en-2,2'(1'H)-naphthalin]-1'-on Structure

3',4'-Dihydrosp...

~%

2-[2-(furan-2-yl)-2-oxoethyl]-3,4-dihydro-2H-naphthalen-1-one Structure

2-[2-(furan-2-y...

2-methylidene-2,3-dihydro-1H-inden-1-one Structure

2-methylidene-2...

Propionaldehyde Structure

Propionaldehyde

~75%

2-(2-oxobutyl)-2,3-dihydroinden-1-one Structure

2-(2-oxobutyl)-...

2-[(dimethylamino)methyl]-2,3-dihydroinden-1-one Structure

2-[(dimethylami...

~%

2-(2-oxobutyl)-2,3-dihydroinden-1-one Structure

2-(2-oxobutyl)-...

Spiro(bicyclo(2.2.1)hept-5-en-2,2'-indan)-1'-on Structure

Spiro(bicyclo(2...

~%

2-(2-oxobutyl)-2,3-dihydroinden-1-one Structure

2-(2-oxobutyl)-...