Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline

[Display omitted] The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy inclu...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron: asymmetry Vol. 27; no. 6; pp. 261 - 267
Main Authors Hiremath, Mahanthaswamy, Sunil Kumar, Yalechakanahalli C., Umashankara, Muddegowda, Sandhya, Nagarakere C., Chandrappa, Siddapa, Pavan Kumar, Chottanahalli S., Mantelingu, Kempegowda, Rangappa, Kanchugarakoppalu S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.04.2016
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ANTIFUNGAL AGENT
CONSTITUENT
ECHINOCANDIN-B
ASYMMETRIC-SYNTHESIS
L-671,329
FERMENTATION
AMINO-ACID (2S,3S,4S)-3-HYDROXY-4-METHYLPROLINE
EFFICIENT
DERIVATIVES
ALKALOIDS
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy include enzymatic separation of an α-methyl β-amino alcohol, Sharpless asymmetric dihydroxylation of an α,β-unsaturated δ-amino ester, and intramolecular cyclization of a sulfonate to a pyrrolidine ring system. Two stereoisomers were synthesized from the common α,β-unsaturated δ-amino ester intermediate. This protocol is simple, straightforward, efficient, highly stereoselective, and economically viable.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2016.02.008