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Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences

Author:
Cordes, Jens, Calo, Frederick, Anderson, Katie, Pfaffeneder, Toni, Laclef, Sylvain, White, Andrew J. P., Barrett, Anthony G. M.
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 652-657
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, geraniol, migratory behavior, organic chemistry, palladium, regioselectivity
Abstract:
A five-step synthesis of the natural product angelicoin A using a late stage highly regioselective palladium(0)-catalyzed decarboxylative prenyl migration and aromatization sequence as the key step is reported. The method was extended with geranyl migration in eight-step total syntheses of hericenone J and hericenol A from geraniol.
Agid:
5498708