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Biomimetic Synthesis of (+)-Aspergillin PZ.

ABSTRACT: The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin?D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels-Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.

SUBMITTER: Reyes JR

PROVIDER: S-EPMC6417427 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Biomimetic Synthesis of (+)-Aspergillin PZ.

Reyes Julius R JR Winter Nils N Spessert Lukas L Trauner Dirk D

Angewandte Chemie (International ed. in English) 20181102 47

The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels-Alder reaction that features high regio- and stereoselectivity. So ...[more]

PMID: 30239081

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