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Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

✍ Scribed by Kenji Mori; Tôru Nakayama; Masayuki Sakuma

Book ID
103992251
Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
755 KB
Volume
4
Category
Article
ISSN
0968-0896

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✦ Synopsis

Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, 1c with a fluorine substituent instead of the chlorine and 1d with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that 1a and 1c are active, while 1b and 1d are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active.

📜 SIMILAR VOLUMES

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

Pheromone Synthesis, CLI. Synthesis of C
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.
✍ Mori, Kenji ;Fukamatsu, Kunio ;Kido, Masaru 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 662 KB

## 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 pa

Pheromone Synthesis, CLXXX. Synthesis of
Pheromone Synthesis, CLXXX. Synthesis of (3S,11S)-3,11-Dimethyl-2-heptacosannone, a New Component of the Female Sex Pheromone of the German Cockroach
✍ Takikawa, Hirosato ;Fujita, Ken ;Mori, Kenji 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 620 KB

## Abstract (3__S__,11__S__)‐3,11‐Dimethyl‐2‐heptacosanone (1), a new and the fourth component of the female sex pheromone of __Blattella germanica__, was synthesized by starting from ethyl (__R__)‐3‐hydroxybutanoate (2) and (__R__)‐citronellol (3).