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Synthesis 2006(16): 2743-2747  
DOI: 10.1055/s-2006-942489
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of the 18-Methoxycoronaridine Side-Chain Precursor

Matthew P. Rainka, Matthew S. Dowling, Chi-Hsin R. King, Harold Meckler, R. Jason Herr*
Medicinal Chemistry and Chemical Development Departments, Albany Molecular Research, Inc., P.O. Box 15098, Albany, NY 12212-5098, USA
e-Mail: rjason.herr@albmolecular.com;
Further Information

Publication History

Received 23 March 2006
Publication Date:
12 July 2006 (online)

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Abstract

An efficient synthesis of the side-chain precursor crucial to the preparation of 18-methoxycoronaridine (18-MC) has been developed. This procedure represents an improvement upon the original synthesis, in which regioisomers were separated by chromatography to provide the requisite precursor. Incorporation of the protected primary alcohol moiety in the early stages of the synthesis provides the requisite regioisomer unambiguously and obviates the need for chromatography at any point.

Key words

18-methoxycoronaridine - 18-MC - debenzylation