N. N. Joshi, V. R. Mamdapur, M. Chadha
1984
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
Abstract Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated. The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials. Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the desired pheromone (1a + 1b). The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3. A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.