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Pheromone Synthesis, CLI. Synthesis of Chlorinated Steroids Related to the Structures Proposed for Blattellastanosides A and B, the Aggregation Pheromone of the German Cockroach, Blattella germanica L.
Author(s) -
Mori Kenji,
Fukamatsu Kunio,
Kido Masaru
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301107
Subject(s) - german cockroach , pheromone , chemistry , sex pheromone , cockroach , german , stereochemistry , zoology , botany , ecology , biology , history , archaeology
Remote functionalization of 5α‐stigmastan‐3β‐ol ( 5 ) to yield eventually 5α‐stigmast‐9(11)‐en‐3α‐ol ( 8 ) was employed for the syntheses of 9α‐chloro‐5α‐stigmastane‐3β,11β‐diol ( 13 ) and 12α‐chloro‐9α,11α‐epoxy‐5α‐stigmastan‐3β‐yl β‐ D ‐glucopyranoside ( 3 ). The former ( 13 ) was the aglycone part of the structure 2 originally proposed for blattellastanoside B, and the latter ( 3 ) was exactly the structure proposed for blattellastanoside A, the components of the aggregation pheromone of the German cockroach, Blattella germanica L. The present work disproved the structures 1 – 4 proposed for blattellastanosides A and B.