(-) SCLEROPHYTIN A

.

 

 

(−)-Sclerophytin A

• Molecular FormulaC₂₀H₃₄O₄
• Average mass338.482 Da
• Monoisotopic mass338.245697 Da

 

5,12-Epoxybenzocyclodecene-6,9,10-triol, tetradecahydro-6,10-dimethyl-1-methylene-4-(1-methylethyl)-, (4R,4aR,5R,6R,9S,10S,12R,12aR)- [ACD/Index Name]

Sclerophytin A

 

Enantioselective Synthesis of (−)-Sclerophytin A by a Stereoconvergent Epoxide Hydrolysis

Bin Wang, Armando P. Ramirez, Justin J. Slade, and James P. Morken*

Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States

J. Am. Chem. Soc., 2010, 132 (46), pp 16380–16382

DOI: 10.1021/ja108185z......

 http://pubs.acs.org/doi/abs/10.1021/ja108185z

The cytotoxic natural product (−)-sclerophytin A was constructed in 13 steps from geranial. Highlights from the synthesis are a stereoselective Oshima−Utimoto reaction, a Shibata−Baba indium-promoted radical cyclization, and a novel stereoconvergent epoxide hydrolysis.

 


 
//////// http://www.chem.ucla.edu/~jung/pdfs/215.pdf