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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Veröffentlicht in:	Angewandte Chemie International Edition 2013-08, Vol.52 (34), p.9019-9022
Hauptverfasser:	Cherney, Emily C., Green, Jason C., Baran, Phil S.
Format:	Artikel
Sprache:	eng
Schlagworte:	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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container_end_page	9022
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creator	Cherney, Emily C. Green, Jason C. Baran, Phil S.
description	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.
doi_str_mv	10.1002/anie.201304609
format	Article
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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
title	Synthesis of ent-Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates
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