Total synthesis of (-)- and (+)-tedanalactam

Mahesh S Majik; Perunninakulath S Parameswaran; Santosh G Tilve

doi:10.1021/jo901143b

Total synthesis of (-)- and (+)-tedanalactam

J Org Chem. 2009 Aug 21;74(16):6378-81. doi: 10.1021/jo901143b.

Authors

Mahesh S Majik¹, Perunninakulath S Parameswaran, Santosh G Tilve

Affiliation

¹ Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India.

PMID: 19588913
DOI: 10.1021/jo901143b

Abstract

The first stereoselective route providing access to both enantiomers of tedanalactam, a naturally occurring piperidone, has been developed. The stereogenic centers were generated by the use of Sharpless asymmetric dihydroxylation. Tandem oxidation-Wittig reaction and one-pot deprotection, lactamization, and oxirane ring formation are the other key elements.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biological Products / chemical synthesis
Biological Products / chemistry
Hydroxylation
Lactams / chemical synthesis*
Lactams / chemistry*
Piperidones / chemical synthesis*
Piperidones / chemistry*
Stereoisomerism

Substances

Biological Products
Lactams
Piperidones
tedanalactam