Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol toward the total synthesis of aquayamycin

Authors
Matsumoto, T Konegawa, T Yamaguchi, H Nakamura, T Sugai, T Suzuki, K
Citation
T. Matsumoto et al., Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol toward the total synthesis of aquayamycin, SYNLETT, (10), 2001, pp. 1650-1652
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
10
Year of publication
2001
Pages
1650 - 1652
Database
ISI
SICI code
0936-5214(200110):10<1650:LAODOM>2.0.ZU;2-F
Abstract
The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corr esponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of t he protocol to the related cyclohexanetriols is also described.