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Synlett 2009(1): 100-102  
DOI: 10.1055/s-0028-1087373
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (1S,3R,5R,7S)-Sordidin, the Main Component of the Aggregation Pheromone of the Banana Weevil Cosmopolites sordidus

Kamilla Lundhauga, Lars Skattebøl*b, Arne Jørgen Aasena
a School of Pharmacy, University of Oslo, P.O. Box 1068, 0316 Oslo, Norway
b Department of Chemistry, University of Oslo, P.O. Box 1033, 0315 Oslo, Norway
Fax: +47(22)85507; e-Mail: lars.skattebol@kjemi.uio.no;
Further Information

Publication History

Received 27 August 2008
Publication Date:
12 December 2008 (online)

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Abstract

A synthesis of the banana weevil pheromone component (1S,3R,5R,7S)-sordidin starting from (S)-2-(2-ethyl-1,3-dioxolanyl)propan-1-ol and (R)-4-hydroxypentan-2-one is described. No epimerization was observed for the final, intramolecular, acid-catalyzed cyclization step using aqueous oxalic acid.

Key words

pheromone - enzymatic resolution - Grignard reaction - diastereoselectivity

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The ee was determined by GC using a CP Chirasil-DEX CB (25 m × 0.25 mm, 0.25 µm film thickness) fused silica capillary column at isothermic temperatures.

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Spectroscopic Data for 1a
¹H NMR (300 MHz, CDCl3): δ = 0.96 (d, J = 7.0 Hz, 3 H), 0.96 (t, J = 7.5 Hz, 3 H), 1.14 (d, J = 6.1 Hz, 3 H), 1.28 (s,
3 H), 1.18-1.35 (m, 3 H), 1.65 (m, 2 H), 2.13 (dd, J = 8.4, 12.4 Hz, 1 H), 2.31 (m, 1 H), 3.93 (m, 1 H). ¹³C NMR (75 MHz, CDCl3): δ = 8.0, 19.9, 21.9, 26.5, 27.4, 40.1, 44.1, 44.9, 64.5, 78.7, 108.6.