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

Synlett

Total synthesis of pterosines B and C via a photochemical key step

P Wessig, J Teubner

Index: Wessig, Pablo; Teubner, Janek Synlett, 2006 , # 10 p. 1543 - 1546

Full Text: HTML

Citation Number: 34

Abstract

Abstract A total synthesis of pterosines B and C is reported. Starting with a fourfold substituted benzene derivative, the introduction of the remaining substituents is mainly based on Sonogashira couplings followed by different transformations of the ethyne moiety. The key step is a photochemical ring-closure of an α-mesyloxy ketone forming the 1- indanone skeleton.

N/A Structure

~%

rac Pterosin B Structure

N/A Structure

~%

rac Pterosin B Structure

3-ethynyl-2,4,6-trimethylphenethyl acetate Structure

3-ethynyl-2,4,6...

~%

rac Pterosin B Structure

2,4,6-trimethyl-3-((trimethylsilyl)ethynyl)phenethyl acetate Structure

2,4,6-trimethyl...

~%

rac Pterosin B Structure

2,4,6-Trimethylbromobenzene Structure

2,4,6-Trimethyl...

~%

rac Pterosin B Structure

2,4,6-Trimethylphenethylalcohol Structure

2,4,6-Trimethyl...

~%

rac Pterosin B Structure

N/A Structure

~%

rac Pterosin B Structure

2,4,6-trimethyl-3-(2-((methylsulfonyl)oxy)acetyl)phenethyl acetate Structure

2,4,6-trimethyl...

~%

rac Pterosin B Structure

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

~%

rac Pterosin B Structure

5,7-dimethyl-6-[2'-hydroxyethyl]-indan-1-one Structure

5,7-dimethyl-6-...

methyl iodide Structure

~43%

rac Pterosin B Structure

2,4,6-Trimethylbromobenzene Structure

2,4,6-Trimethyl...

~54%

(4-Bromo-3,5-dimethylphenyl)methanol Structure

(4-Bromo-3,5-di...

ETHYLENE OXIDE Structure

2,4,6-Trimethylbromobenzene Structure

2,4,6-Trimethyl...

~99%

2,4,6-Trimethylphenethylalcohol Structure

2,4,6-Trimethyl...

N/A Structure

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

N/A Structure

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

3-ethynyl-2,4,6-trimethylphenethyl acetate Structure

3-ethynyl-2,4,6...

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

2,4,6-trimethyl-3-((trimethylsilyl)ethynyl)phenethyl acetate Structure

2,4,6-trimethyl...

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

2,4,6-Trimethylbromobenzene Structure

2,4,6-Trimethyl...

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

2,4,6-Trimethylphenethylalcohol Structure

2,4,6-Trimethyl...

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

N/A Structure

~%

2-(4,6-dimethyl-3-oxo-1,2-dihydroinden-5-yl)ethyl acetate Structure

2-(4,6-dimethyl...

2,6-Xylenol Structure

Carbon dioxide Structure

~34%

4-Hydroxy-3,5-dimethylbenzoic acid Structure

4-Hydroxy-3,5-d...

Ptaquiloside, a potent carcinogen isolated from bracken fern...

[Ojika, Makoto; Wakamatsu, Kazumasa; Niwa, Haruki; Yamada, Kiyoyuki Tetrahedron, 1987 , vol. 43, # 22 p. 5261 - 5274]

Ptaquiloside, a potent carcinogen isolated from bracken fern...

[Ojika, Makoto; Wakamatsu, Kazumasa; Niwa, Haruki; Yamada, Kiyoyuki Tetrahedron, 1987 , vol. 43, # 22 p. 5261 - 5274]