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First Asymmetric Synthesis of (+)-Sordidin and (–)-7-epi-Sordidin, Aggregation Pheromones of the Banana Weevil Cosmopolites sordidus

✍ Scribed by Dieter Enders; Irene Breuer; Anja Nühring

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
137 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The asymmetric synthesis of (1__S__,3__R__,5__R__,7__S__)‐(+)‐sordidin and 7‐epi‐(1__S__,3__R__,5__R__,7__R__)‐(–)‐sordidin, both components of the natural male‐produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2‐dimethyl‐1,3‐dioxan‐5‐one is described. Two of the stereogenic centers were generated by three α‐alkylations of the corresponding RAMP‐hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza‐enolate of 3‐pentanone SAEP‐hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C‐7 epimers in good overall yield (39 %) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97 %, ee ≥ 98 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Pheromone Synthesis, CLXXXIV. Synthesis
Pheromone Synthesis, CLXXXIV. Synthesis and Absolute Configuration of Sordidin, the Male-Produced Aggregation Pheromone of the Banana Weevil,cosmopolites sordidus
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## Abstract The racemate as well as both the enantiomers of sordidin (1‐ethyl‐3,5,7‐trimethyl‐2,8‐dioxabicyclo[3.2.1])octane were synthesized, and the natural pheromone was shown to be (1__S__,3__R__,5__R__,7__S__)‐(+)‐1.

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v