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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Spectroscopic
Data for 1a
¹ H 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, J = 8.4, 12.4
Hz, 1 H), 2.31 (m, 1 H), 3.93 (m, 1 H). ¹³ C
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.
