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Paper | Special issue | Vol 70, No. 1, 2006, pp.279-294
Published online, 15th September, 2006
DOI: 10.3987/COM-06-S(W)20
Synthesis of (+)-Myrtopsine, (+)-7,8-Dimethoxymyrtopsine, and Related 2,3-Dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran Natural Products

Barry B. Snider* and Xiaoxing Wu

*Department of Chemistry, Brandeis University, 415 South Street, Waltham, MA 02254-9110, U.S.A.

Abstract

The first syntheses of myrtopsine (8t) and 7,8-dimethoxymyrtopsine (9t) have been carried out by halogen-metal exchange of 3-iodo-4-methoxyquinolin-2(1H)-ones (15) and (21) with i PrMgCl followed by addition of 3,3-dimethyloxirane-2-carboxaldehyde. A two-step sequence leads selectively to trans-2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofurans (7t), (8t), (9t), (28), and (32) by conversion of a 2-iodophenol or a 3-iodo-4-methoxyquinolin-2(1H)-one to an aryl Grignard reagent and addition of 3-methyl-2-butenal, followed by threo selective epoxidation of the resulting allylic alcohol and cyclization with inversion.