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Cyclodepsipeptide alveolaride C: total synthesis and structural assignment

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Abstract

First stereoselective total synthesis of naturally occurring bioactive cyclodepsipeptide alveolaride C has been achieved using a convergent approach. This synthetic study enabled us to establish unambiguously the stereochemistry of three unassigned chiral centres embedded in the nonpeptidic segment as well as revised the stereochemistry of the proposed β-phenylalanine counterpart of the molecule. The key strategic features of this synthesis include Sharpless asymmetric dihydroxylation for installing the vicinal diol moiety, Julia–Kocienski olefination for constructing the aliphatic side chain, the Shiina protocol for intermolecular esterification, amide coupling and macrolactamization for the ring formation.

Graphical abstract: Cyclodepsipeptide alveolaride C: total synthesis and structural assignment

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Supplementary files

Article information


Submitted
15 Aug 2020
Accepted
17 Sep 2020
First published
21 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Cyclodepsipeptide alveolaride C: total synthesis and structural assignment

S. Saha, D. Paul and R. K. Goswami, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC04478D

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