SYNTHESIS OF (+/-)-PHYLLANTHOCIN VIA A METAL-CATALYZED CYCLOREDUCTION

被引:45
作者
TROST, BM
EDSTROM, ED
机构
[1] Department of Chemistry, Stanford University, Stanford, California
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 05期
关键词
D O I
10.1002/anie.199005201
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cycloreduction of the enyne 2 to a precursor of the title compound 1 is the key step in a total synthesis of 1. The reaction occurs under Pd catalysis with a yield of 86%. This is a case in which the Alder ene reaction proved unsuccessful. Compound 1 is the aglycone of the clinically interesting antitumor agent phyllanthoside (TIPS = iPr3Si). (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany
引用
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页码:520 / 522
页数:3
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共 31 条
[1]   DITERPENE CHEMISTRY .2. PREFERENTIAL OXIDATION OF VINYL GROUPS OF PIMARIC AND SANDARACOPIMARIC ACIDS [J].
APSIMON, JW ;
CHAU, ASY ;
CRAIG, WG ;
KREHM, H .
CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (13) :1439-&
[2]   CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].
BROWN, HC ;
BHAT, KS ;
RANDAD, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576
[3]   TOTAL SYNTHESIS OF (+)-PHYLLANTHOCIN [J].
BURKE, SD ;
COBB, JE ;
TAKEUCHI, K .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3420-3421
[4]   STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].
COREY, EJ ;
CHO, H ;
RUCKER, C ;
HUA, DH .
TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458
[5]   THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION [J].
CUNICO, RF ;
BEDELL, L .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4797-4798
[6]   ESTERFICATION OF ALLYLIC ALCOHOLS WITH BENZOIC-ACID IN PRESENCE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE [J].
GRYNKIEWICZ, G ;
BURZYNSKA, H .
TETRAHEDRON, 1976, 32 (17) :2109-2111
[7]   ACYCLIC STEREOSELECTION .22. DIASTEREOFACIAL SELECTIVITY IN THE LEWIS ACID MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALDEHYDES AND ENONES [J].
HEATHCOCK, CH ;
KIYOOKA, S ;
BLUMENKOPF, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4214-4223
[8]   SYNTHETIC STUDY OF (+ OR -)-CANADENSOLIDE AND RELATED DILACTONES - DOUBLE LACTONIZATION OF UNSATURATED DICARBOXYLIC-ACIDS VIA ACYL HYPOIODITE INTERMEDIATES [J].
KATO, M ;
KAGEYAMA, M ;
TANAKA, R ;
KUWAHARA, K ;
YOSHIKOSHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13) :1932-1941
[9]   TUMOR INHIBITORS .120. PHYLLANTHOCIN, A NOVEL BISABOLANE AGLYCONE FROM ANTILEUKEMIC GLYCOSIDE, PHYLLANTHOSIDE [J].
KUPCHAN, SM ;
LAVOIE, EJ ;
BRANFMAN, AR ;
FEI, BY ;
BRIGHT, WM ;
BRYAN, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (09) :3199-3201
[10]   CHEMICAL-REACTIONS ON CLAYS [J].
LASZLO, P .
SCIENCE, 1987, 235 (4795) :1473-1477