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Synthesis of Mulinane Diterpenoids

Author:
Reber, Keith P., Xu, Jing, Guerrero, Carlos A.
Source:
Journal of organic chemistry 2015 v.80 no.4 pp. 2397-2406
ISSN:
1520-6904
Subject:
chemical structure, dehydrogenation, diastereoselectivity, diterpenoids, organic chemistry, oxidation
Abstract:
The mulinane class of diterpenoids is a set of tricyclic (5-6-7), biologically active natural products whose members exhibit a variety of oxidation states. Herein, we report the inaugural synthesis of four mulinanes employing a divergent approach that relies on a diastereoselective anionic oxy-Cope rearrangement to set the relative configuration of the C8 stereocenter and an unprecedented vinylogous Saegusa dehydrogenation reaction to address C-ring functionality.
Agid:
5505120