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A simple, short, and flexible synthesis of viridiofungin derivatives

A simple, short, and flexible synthesis of viridiofungin derivatives
A simple, short, and flexible synthesis of viridiofungin derivatives
Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C?C bond-forming steps
0022-3263
6185-6191
Goldup, Stephen M.
27165d3a-d39f-4259-a83c-ac5fdd38ad57
Pilkington, Christopher J.
090f9e7e-bb56-4989-abac-d9e0588c919c
White, Andrew J.P.
09c64321-ac83-40be-a22c-3d62e4b19a7e
Burton, Andrew
af718b29-3d32-417b-a0df-4f64aeb3febd
Barrett, Anthony G.M.
72677724-3345-4fd5-b241-d536f0488d71
Goldup, Stephen M.
27165d3a-d39f-4259-a83c-ac5fdd38ad57
Pilkington, Christopher J.
090f9e7e-bb56-4989-abac-d9e0588c919c
White, Andrew J.P.
09c64321-ac83-40be-a22c-3d62e4b19a7e
Burton, Andrew
af718b29-3d32-417b-a0df-4f64aeb3febd
Barrett, Anthony G.M.
72677724-3345-4fd5-b241-d536f0488d71

Goldup, Stephen M., Pilkington, Christopher J., White, Andrew J.P., Burton, Andrew and Barrett, Anthony G.M. (2006) A simple, short, and flexible synthesis of viridiofungin derivatives. Journal of Organic Chemistry, 71 (16), 6185-6191. (doi:10.1021/jo060931e).

Record type: Article

Abstract

Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C?C bond-forming steps

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More information

Published date: June 2006
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 370670
URI: http://eprints.soton.ac.uk/id/eprint/370670
ISSN: 0022-3263
PURE UUID: 9e90babf-499e-495e-875e-b561cd419ce7

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Date deposited: 03 Nov 2014 13:59
Last modified: 14 Mar 2024 18:20

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Contributors

Author: Stephen M. Goldup
Author: Christopher J. Pilkington
Author: Andrew J.P. White
Author: Andrew Burton
Author: Anthony G.M. Barrett

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