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Total Synthesis and Structural Reassignment of Laingolide A.

ABSTRACT: The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.

SUBMITTER: Wu F

PROVIDER: S-EPMC8145716 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Total Synthesis and Structural Reassignment of Laingolide A.

Wu Fusong F Zhang Tao T Yu Jie J Guo Yian Y Ye Tao T

Marine drugs 20210427 5

The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide. ...[more]

PMID: 33925490

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