TOWARDS THE TOTAL SYNTHESIS OF CLERODIN .1.

被引:9
作者
BOUCHARD, H [1 ]
RENARD, PY [1 ]
LALLEMAND, JY [1 ]
机构
[1] ECOLE POLYTECH,SYNTHESE ORGAN LAB,F-91128 PALAISEAU,FRANCE
关键词
CLERODIN; ANTIFEEDANT; STEREOSPECIFIC CLAISEN REARRANGEMENT; QUATERNARY ASYMMETRIC CARBON; TERPENE;
D O I
10.1016/S0040-4039(00)79435-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereo- and enantioselective approach to clerodin 1, an insect antifeedant, is described. The key step involved the stereospecific formation of the C-9-C-11 bond, at an early stage of the synthesis, using a Claisen rearrangement.
引用
收藏
页码:5953 / 5956
页数:4
相关论文
共 19 条
[1]   A SIMPLE ACCESS TO A TRANS-DECALIN EPOXY-DIACETATE, A MODEL OF CLERODIN [J].
BOUCHARD, H ;
LALLEMAND, JY .
TETRAHEDRON LETTERS, 1990, 31 (36) :5151-5152
[2]  
BOUCHARD H, 1991, TETRAHEDRON LETT, V32, P5957, DOI 10.1016/S0040-4039(00)79436-6
[3]   REACTIVITY OF MONOTHIOSELENOACETALS AND MONOSELENOACETALS TOWARDS OXIDATION IN THE SYNTHESIS OF SUBSTITUTED 2,3-DIHYDROFURANS [J].
BRUNETIERE, AP ;
LALLEMAND, JY .
TETRAHEDRON LETTERS, 1988, 29 (18) :2179-2182
[4]   STEREOCHEMICAL ASPECTS OF SOME CLAISEN REARRANGEMENTS WITH CYCLIC ORTHOESTERS [J].
CAVE, RJ ;
LYTHGOE, B ;
METCALFE, DA ;
WATERHOUSE, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10) :1218-1228
[5]   ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION [J].
IRELAND, RE ;
MUELLER, RH ;
WILLARD, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2868-2877
[6]   TOTAL SYNTHESIS OF THE INSECT ANTIFEEDANT AJUGARIN-I AND DEGRADATION STUDIES OF RELATED CLERODANE DITERPENES [J].
JONES, PS ;
LEY, SV ;
SIMPKINS, NS ;
WHITTLE, AJ .
TETRAHEDRON, 1986, 42 (23) :6519-6534
[7]   STEREOCONTROLLED SYNTHESIS OF CLERODIN HOMOLOG - A SYNTHETIC APPROACH TO STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
KOJIMA, Y ;
KATO, N .
TETRAHEDRON, 1981, 37 (15) :2527-2538
[8]   NEW INSECT ECDYSIS INHIBITORY LIMONOID DEACETYLAZADIRACHTINOL ISOLATED FROM AZADIRACHTA-INDICA (MELIACEAE) OIL [J].
KUBO, I ;
MATSUMOTO, A ;
MATSUMOTO, T ;
KLOCKE, JA .
TETRAHEDRON, 1986, 42 (02) :489-496
[9]  
LANDINI D, 1979, CHEM IND-LONDON, P213
[10]   THE TOTAL SYNTHESIS OF THE CLERODANE DITERPENE INSECT ANTIFEEDANT AJUGARIN-I [J].
LEY, SV ;
SIMPKINS, NS ;
WHITTLE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (09) :503-505