Transformation of santonin into(+)-deoxyvernolepin and related dilactones
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2833-2838
- https://doi.org/10.1039/p19870002833
Abstract
Ozonolysis followed by acetylation of the (3S,3aS,5aR,9R,9aS,9bS)-5a-hydroxymethyl-2-methoxy-3,9-dimethyl-2,3-decahydronaphtho[1,2-b]furan (7) derived from (–)-α-santonin gave an unexpected product, (3S,3aS,6R,7S,7aS)-7-[(S)-2-formylethyl]-2-methoxy-3-methyloctahydrobenzofuran-6-spiro-3′-furan-5′-one (13), which served as the key intermediate for the synthesis of (+)-deoxyvernolepin (2) and related unsaturated lactones (4)–(6). Some unsaturated lactones obtained were submitted to a preliminary test for antitumour activity.This publication has 1 reference indexed in Scilit:
- Synthesis of sesquiterpene antitumor lactones. 5. Total synthesis of vernolepin. 2. Stereocontrolled synthesis of (.+-.)-vernolepinJournal of the American Chemical Society, 1979