1. SYNTHESIS OF (±)-VITRENAL
- Author
-
Akihiko Matsuo, Hiroshi Nozaki, Shûichi Hayashi, Hideaki Magari, Mitsuru Nakayama, Takeyoshi Takahashi, Hiroshi Hirota, and Seiryû Uto
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,chemistry ,Stereochemistry ,Monoterpene ,Yield (chemistry) ,Acid treatment ,Aldol condensation ,General Chemistry ,Sesquiterpene ,Formyl group ,Aldehyde - Abstract
(±)-Vitrenal (1), a sesquiterpene aldehyde with a novel vitrane skeleton, was synthesized from a monoterpene piperitenone (2) by 12-step reactions in ca. 7% overall yield. 2-Formyl-isocarane, 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.
- Published
- 1982