Scalable, Divergent Synthesis of Meroterpenoids via “Borono-sclareolide”

A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of “borono-sclareolide”, a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-05, Vol.134 (20), p.8432-8435
Main Authors: Dixon, Darryl D, Lockner, Jonathan W, Zhou, Qianghui, Baran, Phil S
Format: Article
Language:English
Subjects:
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Diterpenes - chemical synthesis
Diterpenes - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
Xanthenes - chemical synthesis
Xanthenes - chemistry
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Summary:A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of “borono-sclareolide”, a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permit rapid access to a variety of related meroterpenoids, many of which possess important biological activity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja303937y