Chemistry Letters p. 1143 - 1146 (1982)
Update date:2022-09-26
Topics:
Magari, Hideaki
Hirota, Hiroshi
Takahashi, Takeyoshi
Matsuo, Akihiko
Uto, Seiryu
et al.
(+/-)-Vitrenal (1), a sesquiterpene aldehyde with a novel vitrane skeleton, was synthesized from a monoterpene piperitenone (2) by 12-step reactions in ca. 7percent overall yield. 2-Formylisocarane, derived from 2 via (+/-)-isocaran-2-one was allylated stereospecifically and, after protection of the formyl group, the allyl chain was modified to a 4-methoxy-3-butenyl group.Acid treatment of the masked dialdehydic intermediate yielded 1 by concomitant deprotection and aldol condensation.
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