Convergent Route to ent-Kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α,6α-Diacetoxy-ent-kaura-9(11),16-dien-12,15-dione

The Hoppe’s homoaldol reaction of a cyclo-hexenyl carbamate with an aldehyde followed by an unprecedented BF3·OEt2 mediated intramolecular Mukaiyama–Michael-type reaction affords the tetracyclic core structure of ent-kaurane diterpenoids. The usage of this convergent approach for assembling these na...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-03, Vol.139 (8), p.2932-2935
Main Authors: Zhao, Xiangbo, Li, Wu, Wang, Junjie, Ma, Dawei
Format: Article
Language:English
Subjects:
Diterpenes, Kaurane - chemical synthesis
Diterpenes, Kaurane - chemistry
Molecular Structure
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Summary:The Hoppe’s homoaldol reaction of a cyclo-hexenyl carbamate with an aldehyde followed by an unprecedented BF3·OEt2 mediated intramolecular Mukaiyama–Michael-type reaction affords the tetracyclic core structure of ent-kaurane diterpenoids. The usage of this convergent approach for assembling these natural products is demonstrated by the first asymmetric total syntheses of two highly oxidized ent-kaurane diterpenoids: Lungshengenin D and 1α,6α-diacetoxy-ent-kaura-9­(11),16-dien-12,15-dione.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b00140