STEREOSPECIFIC SYNTHESIS OF SUSPENSOLIDE, A MALE-PRODUCED PHEROMONE OF THE CARIBBEAN FRUIT-FLY, ANASTREPHA-SUSPENSA (LOEW), AND THE MEXICAN FRUIT-FLY, ANASTREPHA LUDENS (LOEW)

被引:8
作者
HIDALGODELVECCHIO, G [1 ]
OEHLSCHLAGER, AC [1 ]
机构
[1] SIMON FRASER UNIV,DEPT CHEM,BURNABY V5A 1S6,BC,CANADA
关键词
D O I
10.1021/jo00096a029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.
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收藏
页码:4853 / 4857
页数:5
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