Synthesis of natural pulvinic acids based on a '[3+2] cyclization-Suzuki cross-coupling' strategy

被引:32
作者
Ahmed, Z [1 ]
Langer, P [1 ]
机构
[1] Univ Rostock, Inst Chem, D-18051 Rostock, Germany
关键词
butenolides; cyclizations; natural products; pulvinic acids; silyl enol ethers;
D O I
10.1016/j.tet.2004.12.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of pulvinic acid natural products were prepared based on Suzuki cross coupling reactions of alpha-hydroxy-gamma-alkylidenebutenolides which are readily available by cyclization of 1,3-bis-silyl enol ethers with oxalyl chloride. The formal total synthesis of pulvinic acid, atromentic acid, gomphidic acid and of 4-hydroxypulvinic acid, 4'-hydroxypulvinic acid and iso-gomphidic acid are reported. In addition, total syntheses of pinastric acid, xerocomic acid and variegatic acid were accomplished. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2055 / 2063
页数:9
相关论文
共 42 条
[1]  
AGARWAL SC, 1964, INDIAN J CHEM, V2, P17
[2]   Suzuki cross-coupling reactions of γ-alkylidenebutenolides:: Application to the synthesis of vulpinic acid [J].
Ahmed, Z ;
Langer, P .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3753-3757
[3]  
AMEKRAZ B, 2003, ANGEW CHEM INT EDIT, V42, P1289
[4]  
AMEKRAZ B, 2003, ANGEW CHEM, V115, P1327
[5]  
[Anonymous], 1987, PROG CHEM ORG NAT PR
[6]   CONSTITUENTS OF HIGHER FUNGI .9. BOVINONE, 2,5-DIHYDROXY-3-GERANYLGERANYL-1,4-BENZOQUINONE FROM BOLETUS (SUILLUS) BOVINUS (LINN EX FR) KUNTZE [J].
BEAUMONT, PC ;
EDWARDS, RL .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2398-&
[7]   CONSTITUENTS OF HIGHER FUNGI .8. BLUEING OF BOLETUS SPECIES . VARIEGATIC ACID A HYDROXYTETRONIC ACID FROM BOLETUS SPECIES AND A REASSESSMENT OF STRUCTURE OF BOLETOL [J].
BEAUMONT, PC ;
EDWARDS, RL ;
ELSWORTHY, GC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (24) :2968-+
[8]   The β-elimination route to stereodefined γ-alkylidenebutenolides [J].
Brückner, R .
CHEMICAL COMMUNICATIONS, 2001, (02) :141-152
[9]   The synthesis of γ-alkylidenebutenolides [J].
Brückner, R .
CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) :679-718
[10]   CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].
CHAN, TH ;
BROWNBRIDGE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538