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Paper | Special issue | Vol 47, No. 2, 1998, pp.921-931
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)101
Studies on Synthesis of Araplysillins via Oxidative Cyclisation of o-Phenolic Oxime-Acid Derivatives Using Phenyliodonium Diacetate

Masatoshi Murakata, Kohei Yamada, and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo,12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan

Abstract

Efficient synthetic approaches of cyclohexadienonespiroisoxazoline-amides (1), which could be useful as intermediates for the synthesis of dibromotyrosine derived marine natural products araplysillins, are described. Direct cyclisation of o-phenolic oxime-amide (5) with phenyliodonium diacetate (PIDA) produced 1. Amidation of cyclohexadienonespiroisoxazoline-acid (6) also took place efficiently to afford 1.