Meldrum's acid-derived thione dienophile in a convergent and stereoselective synthesis of a tetracyclic quassinoid intermediate.

Abstract

An advanced intermediate toward anti-cancer quassinoids has been synthesized using a quadruple diene-transmissive [4+2]-cycloaddition strategy. High convergence is achieved thanks to a regio- and stereoselective hetero-Diels-Alder reaction using a thione. The relative stereochemistry of the final Diels-Alder adduct was controlled by tethered substituents introduced via a highly syn- and gamma-selective vinylogous Mukaiyama aldol.

• Authors: Stéphane Perreault, Claude Spino
• Journal: Organic letters (Org Lett) Vol. 8 Issue 20 Pg. 4385-8 (Sep 28 2006) ISSN: 1523-7060 [Print] United States
• PMID: 16986906 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Dioxanes
• Quassins
• Meldrum's acid

Topics

• Cyclization
• Dioxanes (chemistry)
• Quassins (chemical synthesis)
• Stereoisomerism