Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Jack J. Rogers; Varinder K. Aggarwal

doi:10.1002/ajoc.202100413

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Jack J. Rogers, Varinder K. Aggarwal

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Abstract

Dysoxylactam A is a 17-membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15-17 steps. Using iterative lithiation-borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11-step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.

Original language	English
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Early online date	10 Aug 2021
DOIs	https://doi.org/10.1002/ajoc.202100413
Publication status	E-pub ahead of print - 10 Aug 2021

Bibliographical note

Funding Information:
J.R thanks the Bristol Chemical Synthesis Centre for Doctoral Training and the EPSRC (EP/G036764/1) for funding, and the University of Bristol for a PhD studentship.

Publisher Copyright:
© 2021 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH

Keywords

assembly-line
homologation
lithiation-borylation
macrocyclic synthesis
polyketides

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10.1002/ajoc.202100413

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Cite this

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title = "Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters",

abstract = "Dysoxylactam A is a 17-membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15-17 steps. Using iterative lithiation-borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11-step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.",

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author = "Rogers, {Jack J.} and Aggarwal, {Varinder K.}",

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AU - Rogers, Jack J.

AU - Aggarwal, Varinder K.

N1 - Funding Information: J.R thanks the Bristol Chemical Synthesis Centre for Doctoral Training and the EPSRC (EP/G036764/1) for funding, and the University of Bristol for a PhD studentship. Publisher Copyright: © 2021 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH

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N2 - Dysoxylactam A is a 17-membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15-17 steps. Using iterative lithiation-borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11-step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.

AB - Dysoxylactam A is a 17-membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15-17 steps. Using iterative lithiation-borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11-step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.

KW - assembly-line

KW - homologation

KW - lithiation-borylation

KW - macrocyclic synthesis

KW - polyketides

U2 - 10.1002/ajoc.202100413

DO - 10.1002/ajoc.202100413

M3 - Article (Academic Journal)

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

ER -

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Abstract

Bibliographical note

Keywords

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