Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 9.(1) The Enantioselective Generation of Tetracyclic ABCE Intermediates by a Tandem Condensation, [3,3]-Sigmatropic Rearrangement, and Cyclization Sequence.
J Org Chem
; 62(23): 7950-7960, 1997 Nov 14.
Article
em En
| MEDLINE
| ID: mdl-11671897
ABSTRACT
Reactions of substituted acroleins with the tryptophan-derived benzyl 2-(benzylamino)-3-[3-[2-[(methoxycarbonyl)methyl]indolyl]]propionate gave tetracyclic hexahydro-1H-pyrrolo[2,3-d] intermediates with stereoselective placement of substituents for cyclization to pentacyclic Strychnos alkaloids. The benzyl ester moiety was readily removed by formation of a corresponding nitrile and reduction, thus providing enantioselective syntheses of the tetracyclic compounds.
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MEDLINE
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En
Ano de publicação:
1997
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Article