Abstract
Dual benefit:(+)-Upial, isolated from the sponge Dysidea fragilis (Kaneohe Bay, Hawaii), as a nonisoprenoid sesquiterpene aldehyde lactone, was efficiently synthesized. The key step involved an intramolecular carbonyl–ene reaction, in which the stereocontrolled construction of a bicyclo[3.3.1]nonane ring with five asymmetric carbon centers and the facile introduction of the exo-methylene unit were achieved in a single step (see scheme).
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