Synthesis of a C1-C9 fragment of rhizoxin

R. J. Davenport; A. C. Regan

Synthesis of a C1-C9 fragment of rhizoxin

R. J. Davenport
, A. C. Regan

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

Abstract

A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an α,β-unsaturated δ-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydrogenation was used to set up the cis relative stereochemistry in the saturated δ-lactone ring. (C) 2000 Published by Elsevier Science Ltd.

Original language	English
Pages (from-to)	7619-7622
Number of pages	3
Journal	Tetrahedron Letters
Volume	41
Issue number	40
Publication status	Published - 30 Sept 2000

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title = "Synthesis of a C1-C9 fragment of rhizoxin",

abstract = "A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an α,β-unsaturated δ-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydrogenation was used to set up the cis relative stereochemistry in the saturated δ-lactone ring. (C) 2000 Published by Elsevier Science Ltd.",

author = "Davenport, \{R. J.\} and Regan, \{A. C.\}",

year = "2000",

month = sep,

day = "30",

language = "English",

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pages = "7619--7622",

journal = "Tetrahedron Letters",

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T1 - Synthesis of a C1-C9 fragment of rhizoxin

AU - Davenport, R. J.

AU - Regan, A. C.

PY - 2000/9/30

Y1 - 2000/9/30

N2 - A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an α,β-unsaturated δ-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydrogenation was used to set up the cis relative stereochemistry in the saturated δ-lactone ring. (C) 2000 Published by Elsevier Science Ltd.

AB - A C1-C9 fragment of the antitumour macrolide rhizoxin has been synthesised. An Evans' asymmetric aldol reaction was used to set up the first two chiral centres, and an α,β-unsaturated δ-lactone was then formed on the acyclic system by an intramolecular Wadsworth-Emmons reaction. Stereoselective hydrogenation was used to set up the cis relative stereochemistry in the saturated δ-lactone ring. (C) 2000 Published by Elsevier Science Ltd.

M3 - Article

SN - 1873-3581

VL - 41

SP - 7619

EP - 7622

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Synthesis of a C1-C9 fragment of rhizoxin

Abstract

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