SYNTHESIS OF MONOTERPENE LACTONES, (+)-BOSCHNIALACTONE AND (+)-ISOIRIDOMYRMECIN, STARTING FROM L-(+)-ARABINOSE

被引：22

作者：

TANAKA, D ^{[1
]}

YOSHINO, T ^{[1
]}

KOUNO, I ^{[1
]}

MIYASHITA, M ^{[1
]}

IRIE, H ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC PHARMACEUT SCI,NAGASAKI 852,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 45期

关键词：

D O I：

10.1016/S0040-4020(01)80554-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the preparation of optically active gamma-substituted alpha,beta-unsaturated delta-lactones as the useful chiral building blocks for natural product synthesis, starting from L-(+)-arabinose and synthesis of two monoterpene lactones, (+)-boschnialactone and (+)-isoiridomyrmecin, by the use of these building blocks are described.

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页码：10253 / 10262

页数：10

相关论文

共 20 条

[1] ALICYCLIC CLAISEN REARRANGEMENT - A GENERAL CARBOCYCLE SYNTHESIS BASED ON 4-ATOM-RING CONTRACTIONS OF LACTONES [J].

ABELMAN, MM ;

FUNK, RL ;

MUNGER, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (14) :4030-4032

[2] A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES [J].

ANDO, M ;

OHHARA, H ;

TAKASE, K .

CHEMISTRY LETTERS, 1986, (06) :879-882

[3] NOVEL ROUTE TO SOME BIOLOGICALLY IMPORTANT COMPOUNDS STARTING WITH A COMMON CHIRAL, BICYCLIC, FUSED LACTONE - ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE AND 2 ANTITHROMBOTICS [J].

ARAI, Y ;

KAWANAMI, S ;

KOIZUMI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :2969-2975

[4]

ARAI Y, 1991, CHEM LETT, P1585

[5] AN EXPEDIENT AND STEREOSELECTIVE SYNTHESIS OF (+0-) BOSCHNIALACTONE [J].

CAILLE, JC ;

TABYAOUI, B ;

GUILARD, R ;

BELLAMY, FD .

SYNTHETIC COMMUNICATIONS, 1985, 15 (08) :669-674

[6] IRIDOIDS - STEREOSPECIFIC SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANOID INTERMEDIATES VIA BICYCLO[2.2.1]HEPTANONES [J].

CALLANT, P ;

STORME, P ;

VANDEREYCKEN, E ;

VANDEWALLE, M .

TETRAHEDRON LETTERS, 1983, 24 (51) :5797-5800

[7] IRIDOIDS - NOVEL TOTAL SYNTHESIS OF (+/-)-ISOIRIDOMYRMECIN AND OF (+/-)-VERBENALOL [J].

CALLANT, P ;

ONGENA, R ;

VANDEWALLE, M .

TETRAHEDRON, 1981, 37 (11) :2085-2089

[8] THE CHEMISTRY OF ANTS .1. TERPENOID CONSTITUENTS OF SOME AUSTRALIAN IRIDOMYRMEX SPECIES [J].

CAVILL, GWK ;

FORD, DL ;

LOCKSLEY, HD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1956, 9 (02) :288-293

[9] SYNTHESIS OF D-ISOIRIDOMYRMECIN AND L-ISOIRIDOMYRMECIN AND RELATED COMPOUNDS [J].

CLARK, KJ ;

FRAY, GI ;

JAEGER, RH ;

ROBINSON, R .

TETRAHEDRON, 1959, 6 (03) :217-224

[10] TRICYCLO[3.3.0.02,8]OCTAN-3-ONES - PHOTOCHEMICALLY PREPARED BUILDING-BLOCKS FOR ENANTIOSPECIFIC TOTAL SYNTHESES OF CYCLOPENTANOID NATURAL-PRODUCTS [J].

DEMUTH, M ;

SCHAFFNER, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (11) :820-836