Synthesis of ent-Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-08, Vol.52 (34), p.9019-9022
Main Authors: Cherney, Emily C., Green, Jason C., Baran, Phil S.
Format: Article
Language:English
Subjects:
beyerane
Construction
diterpenes
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes, Kaurane - chemical synthesis
Diterpenes, Kaurane - chemistry
ent-kaurane
Fragmentation
overbred intermediates
Oxidation
Precursors
Synthesis
Terpenes
total synthesis
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201304609