Paclitaxel synthetic studies. A Diels-Alder approach to the A-ring

被引：7

作者：

Carballares, S

Craig, D ^{[1
]}

Lane, CAL

MacKenzie, AR

Mitchell, WP

Wood, A

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, Ctr Chem Synth, London SW7 2AY, England

[2] Pfizer Ltd, Cent Res, Sandwich CT13 9NJ, Kent, England

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 18期

关键词：

D O I：

10.1039/b005533f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly substituted cyclohexenes corresponding to the A-ring of the anti-cancer diterpene natural product paclitaxel are synthesised using a Diels-Alder reaction and decarboxylative elimination as the key steps.

引用

页码：1767 / 1768

页数：2

共 17 条

[1] THE FREE-RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE - A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE [J].

BARTON, DHR ;

CRICH, D ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1985, 41 (19) :4347-4357

[2] OLEFIN SYNTHESIS VIA FRAGMENTATION OF HINDERED ESTER HALIDES [J].

BELLETIRE, JL ;

WALLEY, DR .

TETRAHEDRON LETTERS, 1983, 24 (14) :1475-1476

[3] SULFONE-MEDIATED CYCLOBUTANONE TO ALPHA-ALKOXY-CYCLOPENTANONE RING EXPANSION REACTIONS - SCOPE, LIMITATIONS AND APPLICATIONS [J].

FINCH, H ;

MJALLI, AMM ;

MONTANA, JG ;

ROBERTS, SM ;

TAYLOR, RJK .

TETRAHEDRON, 1990, 46 (13-14) :4925-4950

[4] SKIPPED CYCLIC ENEDIYNES AND DIENEDIYNES .1. SYNTHESIS, SPECTROSCOPIC PROPERTIES, AND REACTIONS OF A NEW HYDROCARBON RING FAMILY [J].

GLEITER, R ;

MERGER, R ;

NUBER, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8921-8927

[5] FIRST TOTAL SYNTHESIS OF TAXOL .2. COMPLETION OF THE C-RING AND D-RING [J].

HOLTON, RA ;

KIM, HB ;

SOMOZA, C ;

LIANG, F ;

BIEDIGER, RJ ;

BOATMAN, PD ;

SHINDO, M ;

SMITH, CC ;

KIM, SC ;

NADIZADEH, H ;

SUZUKI, Y ;

TAO, CL ;

VU, P ;

TANG, SH ;

ZHANG, PS ;

MURTHI, KK ;

GENTILE, LN ;

LIU, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1599-1600

[6] USE OF SAMARIUM DIIODIDE AS AN ALTERNATIVE TO SODIUM MERCURY AMALGAM IN THE JULIA-LYTHGOE OLEFINATION [J].

KECK, GE ;

SAVIN, KA ;

WEGLARZ, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3194-3204

[7] DIELS-ALDER REACTIONS WITH ACTIVATED 4-METHYL-1,3-PENTADIENES [J].

KIENZLE, F ;

MERGELSBERG, I ;

STADLWIESER, J ;

ARNOLD, W .

HELVETICA CHIMICA ACTA, 1985, 68 (05) :1133-1139

[8]

LEY SV, 1994, SYNTHESIS-STUTTGART, P639

[9] TOTAL SYNTHESIS OF (+/-) ISONOOTKATONE - STEREOCHEMICAL STUDIES OF ROBINSON ANNELATION REACTION WITH 3-PENTEN-2-ONE [J].

MARSHALL, JA ;

WARNE, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (01) :178-&

[10] A TOTAL SYNTHESIS OF TAXOL [J].

MASTERS, JJ ;

LINK, JT ;

SNYDER, LB ;

YOUNG, WB ;

DANISHEFSKY, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16) :1723-1726

← 1 2 →