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2000 alkaloids alkaloids U 0600 09 - 196 A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides. — Opti- mized conditions are presented for the stereoselective introduction of an allyl substituent in the β-carboline skeleton. The chiral auxiliary can be removed without racemization at C-1. Product (VIII) represents an intermediate of (+)-pseudoyohimban. — (ITOH, TAKASHI; MATSUYA, YUJI; ENOMOTO, YASUKO; NAGATA, KAZUHIRO; MIYAZAKI, MICHIKO; OHSAWA, AKIO; Synlett (1999) 11, 1799-1801; Sch. Pharm. Sci., Showa Univ., Shinagawa, Tokyo 142, Japan; EN) 1

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Page 1: ChemInform Abstract: A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides

2000 alkaloids

alkaloidsU 0600

09 - 196A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carbolineEmploying Allyltributyltin and Chiral Acyl Chlorides. — Opti-mized conditions are presented for the stereoselective introduction of an allylsubstituent in the β-carboline skeleton. The chiral auxiliary can be removedwithout racemization at C-1. Product (VIII) represents an intermediate of(+)-pseudoyohimban. — (ITOH, TAKASHI; MATSUYA, YUJI; ENOMOTO,YASUKO; NAGATA, KAZUHIRO; MIYAZAKI, MICHIKO; OHSAWA, AKIO;Synlett (1999) 11, 1799-1801; Sch. Pharm. Sci., Showa Univ., Shinagawa,Tokyo 142, Japan; EN)

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