The first synthesis of the epoxide-containing macrolactone nucleus of oximidine I

J E  Harvey; S A  Raw; R J K  Taylor

doi:10.1016/S0040-4039(03)01775-1

The first synthesis of the epoxide-containing macrolactone nucleus of oximidine I

J E Harvey, S A Raw, R J K Taylor

Chemistry

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

Abstract

A synthesis of the epoxydiene-containing macrolide nucleus of oximidine I is reported, starting from commercially available 3-butyn-l-ol. The key macrocyclisation step is achieved using Homer-Wadsworth-Emmons methodology in the presence of an epoxide. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7209-7212
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(03)01775-1
Publication status	Published - 15 Sept 2003

Keywords

oximidine
Horner-Wadsworth-Emmons
epoxide
FORMAL TOTAL-SYNTHESIS
SALICYLIHALAMIDE-A
STEREOCONTROLLED SYNTHESIS
STEREOSELECTIVE SYNTHESIS
ANTITUMOR MACROLIDES
ENAMIDES
(-)-SALICYLIHALAMIDE-A
PRODUCTS

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10.1016/S0040-4039(03)01775-1

Cite this

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title = "The first synthesis of the epoxide-containing macrolactone nucleus of oximidine I",

abstract = "A synthesis of the epoxydiene-containing macrolide nucleus of oximidine I is reported, starting from commercially available 3-butyn-l-ol. The key macrocyclisation step is achieved using Homer-Wadsworth-Emmons methodology in the presence of an epoxide. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "oximidine, Horner-Wadsworth-Emmons, epoxide, FORMAL TOTAL-SYNTHESIS, SALICYLIHALAMIDE-A, STEREOCONTROLLED SYNTHESIS, STEREOSELECTIVE SYNTHESIS, ANTITUMOR MACROLIDES, ENAMIDES, (-)-SALICYLIHALAMIDE-A, PRODUCTS",

author = "Harvey, {J E} and Raw, {S A} and Taylor, {R J K}",

year = "2003",

month = sep,

day = "15",

doi = "10.1016/S0040-4039(03)01775-1",

language = "English",

volume = "44",

pages = "7209--7212",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - The first synthesis of the epoxide-containing macrolactone nucleus of oximidine I

AU - Harvey, J E

AU - Raw, S A

AU - Taylor, R J K

PY - 2003/9/15

Y1 - 2003/9/15

N2 - A synthesis of the epoxydiene-containing macrolide nucleus of oximidine I is reported, starting from commercially available 3-butyn-l-ol. The key macrocyclisation step is achieved using Homer-Wadsworth-Emmons methodology in the presence of an epoxide. (C) 2003 Elsevier Ltd. All rights reserved.

AB - A synthesis of the epoxydiene-containing macrolide nucleus of oximidine I is reported, starting from commercially available 3-butyn-l-ol. The key macrocyclisation step is achieved using Homer-Wadsworth-Emmons methodology in the presence of an epoxide. (C) 2003 Elsevier Ltd. All rights reserved.

KW - oximidine

KW - Horner-Wadsworth-Emmons

KW - epoxide

KW - FORMAL TOTAL-SYNTHESIS

KW - SALICYLIHALAMIDE-A

KW - STEREOCONTROLLED SYNTHESIS

KW - STEREOSELECTIVE SYNTHESIS

KW - ANTITUMOR MACROLIDES

KW - ENAMIDES

KW - (-)-SALICYLIHALAMIDE-A

KW - PRODUCTS

U2 - 10.1016/S0040-4039(03)01775-1

DO - 10.1016/S0040-4039(03)01775-1

M3 - Article

SN - 0040-4039

VL - 44

SP - 7209

EP - 7212

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -