SYNTHESIS OF A NOVEL 6,5-BICYCLIC HEXAHYDROPYRIDAZINE DERIVATIVE

Authors
DRAGOVICH PS TADA H ZHOU R
Citation
Ps. Dragovich et al., SYNTHESIS OF A NOVEL 6,5-BICYCLIC HEXAHYDROPYRIDAZINE DERIVATIVE, Heterocycles, 41(11), 1995, pp. 2487-2498
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
41
Issue
11
Year of publication
1995
Pages
2487 - 2498
Database
ISI
SICI code
0385-5414(1995)41:11<2487:SOAN6H>2.0.ZU;2-T
Abstract
A convergent synthesis of the 6,5-bicyclic hexahydropyridazine derivat ive (3) is described in which (3S)-N-1-Cbz-piperazic acid methyl ester (4) is coupled with the functionalized carboxylic acid fragment (9). The Sharpless asymmetric dihydroxylation reaction (AD) of the 1,1-disu bstituted olefin (6) is utilized in the preparation of 9 and is observ ed to produce the corresponding diol with 44% enantiomeric excess and R stereochemistry.