Asymmetric alpha-alkylation of N'-tert-butanesulfinyl amidines. Application to the total synthesis of (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.
A highly diastereoselective alpha-alkylation of N'-tert-butanesulfinyl amidines has been developed along with methods for converting the alkylation products to enantiomerically enriched amines that incorporate both alpha- and beta-stereocenters. The utility of this chemistry is further demonstrated by the first asymmetric synthesis of the antimicrobial marine natural product (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.
Kochi
Takuya
T
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
Ellman
Jonathan A
JA
D000478:Alkylation; D000578:Amidines / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
C498356:7-amino-7,8-dihydro-alpha-bisabolene; D000578:Amidines; D000588:Amines; D012717:Sesquiterpenes; D013457:Sulfur Compounds