Stereospecific synthesis of S-(-)-trans-verbenol and its antipode by inversion of sterically hindered alcohols.
J Asian Nat Prod Res
; 24(6): 569-576, 2022 Jun.
Article
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| MEDLINE
| ID: mdl-33307797
ABSTRACT
S-(-)-trans-Verbenol (1) and its antipode, R-(+)-trans-verbenol (1') have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols (1 and 1') from commercially available starting materials S-α-pinene and R-α-pinene was reported. The key steps were mainly depended on the effective SN2 stereo-inversion of the hydroxy group of sterically hindered alcohols (3 and 3'), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Gorgojos
/
Alcoholes
Límite:
Animals
Idioma:
En
Revista:
J Asian Nat Prod Res
Asunto de la revista:
BOTANICA
/
QUIMICA
Año:
2022
Tipo del documento:
Article
País de afiliación:
China