Carbohydrate-based routes to salicylate natural products: formal total synthesis of (+)-apicularen A from D-glucal

A  Lewis; I  Stefanuti; S A  Swain; S A  Smith; R J K  Taylor

Carbohydrate-based routes to salicylate natural products: formal total synthesis of (+)-apicularen A from D-glucal

A Lewis, I Stefanuti, S A Swain, S A Smith, R J K Taylor

Chemistry

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

Abstract

A synthesis of apicularen analogue (-)-4 in 18 steps from D-glucal is reported. As (+)-4 has been converted into apicularen A in 8 steps, this constitutes a formal total synthesis of this potent naturally occurring anti-cancer agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	5549-5552
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	32
Publication status	Published - 6 Aug 2001

Keywords

APICULAREN-A
CYTOTOXIC MACROLIDES
ANTITUMOR MACROLIDES
SALICYLIHALAMIDE-A
SIDE-CHAIN
MACROLACTONIZATION
ELUCIDATION
ENAMIDES

Cite this

@article{a46ac92ad72b42e28f1a3a0c3f8ae50c,

title = "Carbohydrate-based routes to salicylate natural products: formal total synthesis of (+)-apicularen A from D-glucal",

abstract = "A synthesis of apicularen analogue (-)-4 in 18 steps from D-glucal is reported. As (+)-4 has been converted into apicularen A in 8 steps, this constitutes a formal total synthesis of this potent naturally occurring anti-cancer agent. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "APICULAREN-A, CYTOTOXIC MACROLIDES, ANTITUMOR MACROLIDES, SALICYLIHALAMIDE-A, SIDE-CHAIN, MACROLACTONIZATION, ELUCIDATION, ENAMIDES",

author = "A Lewis and I Stefanuti and Swain, {S A} and Smith, {S A} and Taylor, {R J K}",

year = "2001",

month = aug,

day = "6",

language = "English",

volume = "42",

pages = "5549--5552",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "32",

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TY - JOUR

T1 - Carbohydrate-based routes to salicylate natural products: formal total synthesis of (+)-apicularen A from D-glucal

AU - Lewis, A

AU - Stefanuti, I

AU - Swain, S A

AU - Smith, S A

AU - Taylor, R J K

PY - 2001/8/6

Y1 - 2001/8/6

N2 - A synthesis of apicularen analogue (-)-4 in 18 steps from D-glucal is reported. As (+)-4 has been converted into apicularen A in 8 steps, this constitutes a formal total synthesis of this potent naturally occurring anti-cancer agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - A synthesis of apicularen analogue (-)-4 in 18 steps from D-glucal is reported. As (+)-4 has been converted into apicularen A in 8 steps, this constitutes a formal total synthesis of this potent naturally occurring anti-cancer agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - APICULAREN-A

KW - CYTOTOXIC MACROLIDES

KW - ANTITUMOR MACROLIDES

KW - SALICYLIHALAMIDE-A

KW - SIDE-CHAIN

KW - MACROLACTONIZATION

KW - ELUCIDATION

KW - ENAMIDES

M3 - Article

SN - 0040-4039

VL - 42

SP - 5549

EP - 5552

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -