FIRST ENANTIOSELECTIVE SYNTHESIS OF (-)-AKAGERINE BY A CHEMOENZYMATICAPPROACH

Authors
DANIELI B LESMA G MAURO M PALMISANO G PASSARELLA D
Citation
B. Danieli et al., FIRST ENANTIOSELECTIVE SYNTHESIS OF (-)-AKAGERINE BY A CHEMOENZYMATICAPPROACH, Journal of organic chemistry, 60(8), 1995, pp. 2506-2513
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
8
Year of publication
1995
Pages
2506 - 2513
Database
ISI
SICI code
0022-3263(1995)60:8<2506:FESO(B>2.0.ZU;2-A
Abstract
(-)-Akagerine (1) was synthesized in an efficient and stereocontrolled fashion from the readily available (1S,2R)-cyclohexenedimethanol mono acetate 4. Key steps were the cleavage of the C(17)/C(18) bond of 14a and the regio- and stereoselective cyclization of the dialdehyde 16 to give the tetracyclic skeleton of akagerine.