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Synthesis of ent ‐Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates
Author(s) -
Cherney Emily C.,
Green Jason C.,
Baran Phil S.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201304609
Subject(s) - polyene , bicyclic molecule , chemistry , terpene , yield (engineering) , stereochemistry , diterpene , organic chemistry , physics , thermodynamics
Efficient access to minimally oxidized members of the ent ‐kaurane and beyerane class of terpenes has been achieved by using a polyene cyclization precursor designed to directly yield oxidation at the axial C19‐methyl group. Construction of the [3.2.1]bicyclic system found in the ent ‐kaurane skeleton was realized with two overbred intermediates. Wagner–Meerwein rearrangement of the [3.2.1]bicyclic system yields the beyerane skeleton of isosteviol.