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

Tetrahedron

Asymmetric total synthesis of natural (-)-and unnatural (+)-steganacin: Determination of the absolute configuration of natural antitumor steganacin

K Tomioka, T Ishiguro, Y Iitaka, K Koga

Index: Tomioka, Kiyoshi; Ishiguro, Tsuneo; Iitaka, Yoichi; Koga, Kenji Tetrahedron, 1984 , vol. 40, # 8 p. 1303 - 1312

Full Text: HTML

Citation Number: 106

Abstract

A virtually complete asymmetric control in the synthesis of 2, 3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide (12) as the chiral acceptor for the conjugate 1, 4-addition. Highly efficient asymmetric total synthesis of natural (-)-and unnatural (+)-steganacin was accomplished. The absolute stereostructure of natural antitumor steganain was determined to be 1.

3-(1,3-benzodioxol-5-ylmethyl)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

3-(1,3-benzodio...

~96%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

S(+)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE Structure

S(+)-DIHYDRO-5-...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

(4S)-(+)-2-phenylseleno-4-trityloxymethyl-butan-4-olide Structure

(4S)-(+)-2-phen...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

2-(3,4,5-trimethoxyphenyl)-1,3-dithiane Structure

2-(3,4,5-trimet...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

5-(Bromomethyl)-1,3-benzodioxole Structure

5-(Bromomethyl)...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

(5S)-5-(trityloxymethyl)-5H-furan-2-one Structure

(5S)-5-(tritylo...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

3,4,5-Trimethoxybenzaldehyde Structure

3,4,5-Trimethox...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

D-erythro-Pentonicacid,2,3-dideoxy-3-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]-5-O-(triphenylmethyl)-,g-lactone Structure

D-erythro-Pento...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

2(3H)-Furanone, dihydro-5-[(phenylmethoxy)methyl]-, (5S)- Structure

2(3H)-Furanone,...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

γ-benzyloxymethyl-α,β-butenolide Structure

γ-benzyloxymeth...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

(+)-(2S,3S,4S)-2-piperonyl-3-(2-(3,4,5-trimethoxyphenyl)-1,3-dithiane-2-yl)-4-benzyloxymethyl-butan-4-olide Structure

(+)-(2S,3S,4S)-...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

(4S)-(+)-2-phenylseleno-4-benzyloxymethyl-butan-4-olide Structure

(4S)-(+)-2-phen...

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

N/A Structure

~%

(2S,3S,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]pentane-1,2,5-triol Structure

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

S(+)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE Structure

S(+)-DIHYDRO-5-...

~%

D-erythro-Pentonicacid,2,3-dideoxy-3-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]-5-O-(triphenylmethyl)-,g-lactone Structure

D-erythro-Pento...

(4S)-(+)-2-phenylseleno-4-trityloxymethyl-butan-4-olide Structure

(4S)-(+)-2-phen...

~%

D-erythro-Pentonicacid,2,3-dideoxy-3-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]-5-O-(triphenylmethyl)-,g-lactone Structure

D-erythro-Pento...

3,4,5-Trimethoxybenzaldehyde Structure

3,4,5-Trimethox...

~%

D-erythro-Pentonicacid,2,3-dideoxy-3-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]-5-O-(triphenylmethyl)-,g-lactone Structure

D-erythro-Pento...

D-erythro-Pentonicacid,2,3-dideoxy-3-[2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]-5-O-(triphenylmethyl)-,g-lactone Structure

D-erythro-Pento...

~63%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

S(+)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE Structure

S(+)-DIHYDRO-5-...

~%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

(4S)-(+)-2-phenylseleno-4-trityloxymethyl-butan-4-olide Structure

(4S)-(+)-2-phen...

~%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

2-(3,4,5-trimethoxyphenyl)-1,3-dithiane Structure

2-(3,4,5-trimet...

~%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

(5S)-5-(trityloxymethyl)-5H-furan-2-one Structure

(5S)-5-(tritylo...

~%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

3,4,5-Trimethoxybenzaldehyde Structure

3,4,5-Trimethox...

~%

(4S,5S)-5-(hydroxymethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one Structure

(4S,5S)-5-(hydr...

(4S)-(+)-2-phenylseleno-4-trityloxymethyl-butan-4-olide Structure

(4S)-(+)-2-phen...

~87%

(5S)-5-(trityloxymethyl)-5H-furan-2-one Structure

(5S)-5-(tritylo...

First asymmetric total synthesis of (+)-steganacin determina...

[Tomioka, Kiyoshi; Ishiguru, Tsuneo; Koga, Kenji Tetrahedron Letters, 1980 , vol. 21, p. 2973 - 2976]