A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines.
J Org Chem
; 72(6): 2212-5, 2007 Mar 16.
Article
in En
| MEDLINE
| ID: mdl-17298097
ABSTRACT
A general and versatile method for the divergent and diastereoselective synthesis of polyhydroxylated indolizidines has been established. The annulation reactions of a readily available enantiopure dihydroxylated cyclic secondary enamine with alpha,beta-unsaturated carboxylates including methyl acrylate, methyl crotonate, methyl 2-hexenoate, allenoate, and dimethyl acetylenedicarboxylate and with malonyl chloride produced hexahydro- or tetrahydro-5-indolizinone-8-carboxylates in high yields. The resulting 5-indolizinone derivatives were converted into diverse polyhydroxylated indolizidines in good yields through practical hydrogenation and reduction reactions.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Indolizines
Language:
En
Journal:
J Org Chem
Year:
2007
Document type:
Article
Affiliation country:
China