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Paper | Regular issue | Vol 89, No. 3, 2014, pp.669-677
Published online, 28th January, 2014
DOI: 10.3987/COM-13-12921
Enantioselective Total Synthesis of (–)-Scabronine D

Yu Kobayakawa and Masahisa Nakada*

*Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The first enantioselective total synthesis of (–)-scabronine D comprising a unique bridged hemiacetal is described. The total synthesis is successfully accomplished using an enantiopure intermediate prepared in the total synthesis of (–)-scabronines G and A, and (–)-episcabronine A. Because the advanced intermediate was found to be sensitive to basic reaction conditions, the C14 keto and C11 hydroxy groups had to be co-protected as methyl acetal. In addition, both the C15 hydroxy and C17 carboxyl groups were too reactive to be chemically discriminated; hence, the carboxyl group once formed was protected as a tert-butyl ester for ensuring successful transformations.