Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A
- 1 June 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (13) , 2001-2004
- https://doi.org/10.1021/ol015976a
Abstract
Pestalotiopsin A is a structurally unique caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalized 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. The approach includes a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate.Keywords
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