Journal of the Chemical Society. Perkin transactions I p. 2833 - 2838 (1987)
Update date:2022-09-26
Topics:
Watanabe, Masataka
Yoshikoshi, Akira
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.
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Doi:10.1021/jm00136a012
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