Synthetic studies on (+)-wortmannin. An asymmetric construction of an allylic quaternary carbon center by a Heck reaction.

被引：28

作者：

Honzawa, S ^{[1
]}

Mizutani, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 02期

关键词：

intramolecular Heck reaction; kinetic resolution;

D O I：

10.1016/S0040-4039(98)02298-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of (+/-)-4 with Pd(OAc)(2), DPPP, TBAB and K2CO3 in toluene gave 16 beta in a highly stereoselective manner (17:1, 90%). Moreover, reaction of (+/-)-4 with Pd(OAc)(2), (R)-Tol-BINAP and K2CO3 in toluene afforded 16 beta in 96% ee and in 20% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：311 / 314

页数：4

共 20 条

[1] ACADI A, 1991, TETRAHEDRON, V47, P1525
[2] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2
AMATORE, C
AZZABI, M
JUTAND, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) : 8375 - 8384
[3] BRIAN PW, 1972, J CHEM SOC CHEM COMM, P1063
[4] PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES
BURNS, B
GRIGG, R
SANTHAKUMAR, V
SRIDHARAN, V
STEVENSON, P
WORAKUN, T
[J]. TETRAHEDRON, 1992, 48 (35) : 7297 - 7320
[5] THE STRUCTURE AND FUNCTION OF ESTROGENS .3. 3,17-BETA-DIHYDROXY-6-OXAOESTRA-1,3,5(10),8(9)-TETRAEN-7-ONE AND RELATED STEROIDAL COUMARINS
CASELLI, AS
COLLINS, DJ
STONE, GM
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (04) : 799 - 808
[6] SYNTHESES OF INSECT JUVENILE-HORMONE
COCHRANE, JS
HANSON, JR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (03): : 361 - &
[7] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
DE MEIJERE, A
MEYER, FE
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411
[8] 17-BETA-HYDROXYWORTMANNIN - A POTENT INHIBITOR OF BONE-RESORPTION AND PHOSPHATIDYLINOSITOL-3-KINASE
DODGE, JA
BRYANT, HU
KIM, J
MATTER, WF
NORMAN, BH
SRINIVASAN, U
VLAHOS, CJ
SATO, M
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (15) : 1713 - 1718
[9] PALLADIUM-CATALYZED VINYLATION OF ORGANIC HALIDES UNDER SOLID LIQUID-PHASE TRANSFER CONDITIONS
JEFFERY, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) : 1287 - 1289
[10] TETRAALKYLAMMONIUM SALTS IN HECK-TYPE REACTIONS USING AN ALKALI-METAL HYDROGEN CARBONATE OR AN ALKALI-METAL ACETATE AS THE BASE
JEFFERY, T
GALLAND, JC
[J]. TETRAHEDRON LETTERS, 1994, 35 (24) : 4103 - 4106

← 1 2 →