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. 2011 Aug 5;13(15):3920-3.
doi: 10.1021/ol201443k. Epub 2011 Jul 12.

Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor

Prasoon Gupta  1 , Upasana Sharma, Thomas C Schulz, Eric S Sherrer, Amanda B McLean, Allan J Robins, Lyndon M West
Affiliations

Bioactive diterpenoid containing a reversible "spring-loaded" (E,Z)-dieneone Michael acceptor

Prasoon Gupta et al. Org Lett. .

Abstract

Three new briarane diterpenoids, briareolate esters L-N (1-3), have been isolated from a gorgonian Briareum asbestinum. Briareolate esters L (1) and M (2) are the first natural products possessing a 10-membered macrocyclic ring with a (E,Z)-dieneone and exhibit growth inhibition activity against both human embryonic stem cells (BG02) and a pancreatic cancer cell line (BxPC-3). Briareolate ester L (1) was found to contain a "spring-loaded" (E,Z)-dieneone Michael acceptor group that can form a reversible covalent bond to model sulfur-based nucleophiles.

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Figures

Figure 1
Figure 1
Selected 2D NMR correlations for 1.
Figure 2
Figure 2
Optimized molecular structure of briareolate L (1).
See this image and copyright information in PMC

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