Total Synthesis of Icumazole A Using a Modified Cadiot-Chodkiewicz Coupling

Jack Buntine; Samrat Dasgupta; Keely Dorney; Oscar Rubinstein; Mina Salimimarand; Jonathan M. White; Mark A. Rizzacasa

doi:10.1021/acs.orglett.3c04268

Total Synthesis of Icumazole A Using a Modified Cadiot-Chodkiewicz Coupling

Jack Buntine, Samrat Dasgupta, Keely Dorney, Oscar Rubinstein, Mina Salimimarand, Jonathan M. White, Mark A. Rizzacasa

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

Abstract

The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels-Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot-Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.

Original language	English
Pages (from-to)	1062-1066
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.3c04268
Publication status	Published or Issued - 9 Feb 2024
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c04268

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title = "Total Synthesis of Icumazole A Using a Modified Cadiot-Chodkiewicz Coupling",

abstract = "The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels-Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot-Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.",

author = "Jack Buntine and Samrat Dasgupta and Keely Dorney and Oscar Rubinstein and Mina Salimimarand and White, {Jonathan M.} and Rizzacasa, {Mark A.}",

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AU - Buntine, Jack

AU - Dasgupta, Samrat

AU - Dorney, Keely

AU - Rubinstein, Oscar

AU - Salimimarand, Mina

AU - White, Jonathan M.

AU - Rizzacasa, Mark A.

PY - 2024/2/9

Y1 - 2024/2/9

N2 - The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels-Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot-Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.

AB - The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels-Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot-Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.

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JO - Organic Letters

JF - Organic Letters

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ER -

Total Synthesis of Icumazole A Using a Modified Cadiot-Chodkiewicz Coupling

Abstract

ASJC Scopus subject areas

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