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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.

✍ Scribed by Mori, Kenji ;Fukamatsu, Kunio ;Kido, Masaru

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 662 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1993199301107

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✦ Synopsis

Abstract

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.

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Pheromone Synthesis, CLII. Synthesis of

Pheromone Synthesis, CLII. Synthesis of Blattellastanosides A and B, Chlorinated Steroid Glucosides Isolated as the Aggregation Pheromone of the German Cockroach,Blattella germanica L.

✍ Mori, Kenji ;Fukamatsu, Kunio ;Kido, Masaru 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 594 KB

## Abstract β‐Sitosterol (3) was converted to blattellastanosides A (1, 6α‐chloro‐4β,5‐epoxy‐5β‐stigmastan‐3β‐yl β‐D‐glucopyranoside) and B (2, 6α‐chloro‐5‐hydroxy‐5β‐stigmastan‐3β‐yl β‐D‐glucopyranoside), the arrestant components of the aggregation pheromone of the German cockroach, __Blattella ge