An efficient asymmetric synthesis of the mercaptopyrrolidine side chain of an important β-methyl carbapenem antibiotic

An efficient asymmetric synthesis of the mercaptopyrrolidine side chain 2 1s described. The β-ketoester 4 is hydrogenated diastereoselectively to give the (R)-β-hydroxyester 5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produc...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 18; pp. 3203 - 3206
Main Authors Armstrong, Joseph D., Keller, Jennifer L., Lynch, Joseph, Liu, Tom, Hartner, Frederick W., Ohtake, Norikazu, Okada, Shigemitsu, Imai, Yasuyuki, Okamoto, Osamu, Ushijima, Ryosuke, Nakagawa, Susumu, Volante, R.P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.05.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
HYDROGENATION
ACID
REDUCTION
CONVERSION
COMPLEXES
CARBOXYLIC ESTERS
HIGHLY EFFICIENT
SULFIDE
AMIDES
Online AccessGet full text

Cover

More Information
Summary:An efficient asymmetric synthesis of the mercaptopyrrolidine side chain 2 1s described. The β-ketoester 4 is hydrogenated diastereoselectively to give the (R)-β-hydroxyester 5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produce 2 in 34% overall yield from BOC-L-trans-4-hydroxyproline methylester 3 (Scheme 1). The asymmetric synthesis of bis-HCl salt 2 of the thiol side chain of BO-2727 is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)00613-8