CATALYTIC IRON-MEDIATED ENE CARBOCYCLIZATIONS OF TRIENES - ENANTIOSELECTIVE SYNTHESES OF THE IRIDOID MONOTERPENES (-)-MITSUGASHIWALACTONE AND (+)-ISOIRIDOMYRMECIN

被引：56

作者：

TAKACS, JM

MYOUNG, YC

机构：

[1] Department of Chemistry, University of Nebraska-Lincoln, Lincoln

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 03期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)74120-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).

引用

收藏

页码：317 / 320

页数：4

相关论文

共 23 条

[1] NUCLEOPHILIC-SUBSTITUTION OF FUNCTIONAL ALLYLIC CYCLOALKENOL ACETATES BY ORGANOMETAL COMPOUNDS IN THE PRESENCE OF COPPER-SALTS - APPLICATION TO RAPID SYNTHESIS OF MITSUGASHIWALACTONE [J].

AMRI, H ;

RAMBAUD, M ;

VILLIERAS, J .

TETRAHEDRON, 1990, 46 (10) :3535-3546

[2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

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

CALLANT, P ;

ONGENA, R ;

VANDEWALLE, M .

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

[4] 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

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[6] THE TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTICS - A CONVERGENT SYNTHESIS OF LASALOCID-A (X537A) [J].

IRELAND, RE ;

ANDERSON, RC ;

BADOUD, R ;

FITZSIMMONS, BJ ;

MCGARVEY, GJ ;

THAISRIVONGS, S ;

WILCOX, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :1988-2006

[7] STEREOSELECTIVE TANDEM RADICAL CYCLIZATIONS - SYNTHESIS OF ISOIRIDOMYRMECIN [J].

KILBURN, JD .

TETRAHEDRON LETTERS, 1990, 31 (15) :2193-2196

[8]

Mikami K, 1989, SYNLETT, P45

[9] IMPROVED ROUTE TO 3-VINYL-SUBSTITUTED CYCLOPENTANONES - SYNTHESIS OF (+/-)-MITSUGASHIWALACTONE [J].

NUGENT, WA ;

HOBBS, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3376-3378

[10]

OHTA H, 1977, J ORG CHEM, V42, P12312