Biomimetic Synthesis of (+)-Aspergillin PZ

Julius R. Reyes; Nils Winter; Lukas Spessert; Dirk Trauner

doi:10.1002/anie.201809703

Biomimetic Synthesis of (+)-Aspergillin PZ

Julius R. Reyes, Nils Winter, Lukas Spessert, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	15587-15591
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	47
DOIs	https://doi.org/10.1002/anie.201809703
State	Published - Nov 19 2018

Keywords

Diels–Alder cycloaddition
biomimetic synthesis
cytochalasans
high-pressure chemistry
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201809703

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title = "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.",

keywords = "Diels–Alder cycloaddition, biomimetic synthesis, cytochalasans, high-pressure chemistry, total synthesis",

author = "Reyes, {Julius R.} and Nils Winter and Lukas Spessert and Dirk Trauner",

note = "Funding Information: We thank the Deutsche Forschungsgemeinschaft (SFB 749), the Alexander von Humboldt Stiftung, and the National Institutes of Health (1R01GM126228) for financial support of this work. J.R.R. is grateful to the Alexander von Humboldt Stiftung and the Carl Friedrich von Siemens Stiftung for a postdoctoral fellowship. We thank Dr. Peter Mayer (LMU Munich) for X-ray structure analysis and Martin Maier (NYU) and Dr. Giulio Volpin (NYU) for computational analysis of aspergillin PZ. Furthermore, Dr. Antonio Rizzo (Seoul National University), Dr. Felix Hartrampf (Boston College) and Prof. Dr. Hong-Dong Hao (Northwest A&F University) are warmly acknowledged for insightful discussions.",

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AU - Trauner, Dirk

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