Total synthesis of pederin

John C. Jewett; Viresh H. Rawal

doi:10.1002/anie.200701677

Total synthesis of pederin

John C. Jewett, Viresh H. Rawal

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

68 Scopus citations

Abstract

(Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero-Diels-Alder reaction of a hindered diene, a Mukaiyama-Michael reaction to set two additional stereocenters, and a Curtius rearrangement to stereospecifically introduce the aminal functionality.

Original language	English (US)
Pages (from-to)	6502-6504
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	34
DOIs	https://doi.org/10.1002/anie.200701677
State	Published - 2007
Externally published	Yes

Keywords

Curtius rearrangement
Diastereoselectivity
Mukaiyama-Michael reaction
Natural products
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200701677

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keywords = "Curtius rearrangement, Diastereoselectivity, Mukaiyama-Michael reaction, Natural products, Total synthesis",

author = "Jewett, {John C.} and Rawal, {Viresh H.}",

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AU - Rawal, Viresh H.

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AB - (Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero-Diels-Alder reaction of a hindered diene, a Mukaiyama-Michael reaction to set two additional stereocenters, and a Curtius rearrangement to stereospecifically introduce the aminal functionality.

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KW - Diastereoselectivity

KW - Mukaiyama-Michael reaction

KW - Natural products

KW - Total synthesis

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Total synthesis of pederin

Abstract

Keywords

ASJC Scopus subject areas

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