A MICROBIAL LIPASE BASED STEREOSELECTIVE SYNTHESIS OF (D)-ALPHA-TOCOPHEROL FROM (R)-CITRONELLAL AND )-(6-HYDROXY-2,5,7,8-TETRAMETHYLCROMAN-2-YL)ACETIC ACID

Authors
COFFEN DL COHEN N PICO AM SCHMID R SEBASTIAN MJ WONG F
Citation
Dl. Coffen et al., A MICROBIAL LIPASE BASED STEREOSELECTIVE SYNTHESIS OF (D)-ALPHA-TOCOPHEROL FROM (R)-CITRONELLAL AND )-(6-HYDROXY-2,5,7,8-TETRAMETHYLCROMAN-2-YL)ACETIC ACID, Heterocycles, 39(2), 1994, pp. 527-552
Citations number
73
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
39
Issue
2
Year of publication
1994
Pages
527 - 552
Database
ISI
SICI code
0385-5414(1994)39:2<527:AMLBSS>2.0.ZU;2-B
Abstract
A new synthesis of natural vitamin E (2R,4'R,8'R)-alpha-tocopherol) ba sed on (R)-citronellal and -(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl )acetic acid is described. The citronellal is elaborated into an optic ally pure C-13 allylic carbonate using a lipase catalyzed kinetic reso lution to control the new chiral center. Palladium catalyzed coupling of this C-13 carbonate with either a beta-ketoester or beta-ketosulpho ne derived from the chromanylacetic acid completes the assembly of the alpha-tocopherol skeleton. Appropriate functional group modifications are used to complete the synthesis.