Synthesis of the Enatiomers of Lasiol, the Major Volatile Component of the Mandibular Gland Secretion ofLasius meridionalis
β Scribed by Kuwahara, Shigefumi ;Shibata, Yasuo ;Hiramatsu, Akira
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 275 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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β¦ Synopsis
Abstract
Both enantiomers of lasiol, erythroβ2,3,6βtrimethylβ5βheptenβ1βol (1), were synthesized in 6 steps from the enantiomers of 3βmethylβ4βbutanolide (2).
π SIMILAR VOLUMES
## Abstract The syntheses of the title compounds (2__R__,6__S__)β**1** and (2__S__,6__R__)β**1** from (__R__)β and (S)βΞ²βhydroxybutyrate **3** are described. The formation of the spiroacetal **1** from (__R__)β**9** proceeded stereoselectively to give only (2__R__,6__S__)β**1**. Similarly (__S__)β*
The title compounds (2R,5S,7R)-1, (2S,5S,7R)-l, (2R,5R,7S)-l, and (2S,5R,7S)-l were synthesized from ethyl (S)-lactate (3) and the (R)-or (S)-enantiomers of ethyl 3-hydroxybutanoate (4a). The formation of the spiro acetal 1 from 2b proceeds stereoselectively. Various spiro acetals with axial S-chira