Synthesis of cruentaren A.

Abstract

Cruentaren A, an antifungal benzolactone produced by the myxobacterium Byssovorax cruenta, is highly cytotoxic against various human cancer cell lines and a highly selective inhibitor of mitochondrial F-ATPase. A convergent and efficient synthesis of cruentaren A is reported, based upon a diastereoselective alkylation, a series of stereoselective aldol reactions utilizing Myers' pseudoephedrine propionamide, an acyl bromide mediated esterification, and a ring-closing metathesis (RCM) as the key steps. The RCM reaction was applied for the first time toward the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.

• Authors: Bhaskar Reddy Kusuma, Gary E L Brandt, Brian S J Blagg
• Journal: Organic letters (Org Lett) Vol. 14 Issue 24 Pg. 6242-5 (Dec 21 2012) ISSN: 1523-7052 [Electronic] United States
• PMID: 23205851 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Antifungal Agents
• Macrolides
• cruentaren A
• Mitochondrial Proton-Translocating ATPases

Topics

• Alkylation
• Antifungal Agents
• Humans
• Macrolides (chemical synthesis, chemistry, pharmacology)
• Mitochondrial Proton-Translocating ATPases (antagonists & inhibitors)
• Molecular Structure
• Myxococcales (chemistry)
• Stereoisomerism