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Synthesis of (2S,3R,1'R)-stegobinone, the pheromone of the drugstore beetle, with stereocontrol at C-2 and C-1'

✍ Scribed by Kenji Mori; Takashi Ebata

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
537 KB
Volume
42
Category
Article
ISSN
0040-4020

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✦ Synopsis

C-3 took place to some extent. The crude 2 was oxidized under the Swern condition to give (2S,3IZ,l'R)-stegobinone 1 in 14.0 % yield from 3 after purification by prep TLC. The unwanted by-product, (2S,3S,l'R)-stegobinone, could be removed by TLC separation. The IR and mass spectral properties of our (2&3&,1'R)-1 coincided with those reported for the natural pheromone.2 The overall yield of (2S,3&l'R)-l was 3.61 % in 18 steps from 6, or 7.86 % in 12 steps from 7. Table 1. CD Spectral data of stegobinone (n-hexane) Natural7 Synthetic (2S,3R,l'R)* (2S,3R,1'RSj6 A 360 nm AE -0.42 -0.

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