Unexpected Diels–Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin

The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels–Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

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Bibliographic Details
Published in:Organic letters 2013-04, Vol.15 (7), p.1748-1751
Main Authors: Suzuki, Takahiro, Miyajima, Yuria, Suzuki, Kaname, Iwakiri, Kanako, Koshimizu, Masaki, Hirai, Go, Sodeoka, Mikiko, Kobayashi, Susumu
Format: Article
Language:English
Subjects:
Biomimetics
Models, Molecular
Molecular Structure
Salicylates - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
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Summary:The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels–Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400549q