Abstract
Reaction of dicyclopropyl cadmium and phthalic acid monochloride monomethyl ester gives o-carboxyphenyl cyclopropyl ketone ( 2). Reaction of the methyl ester of 2 with methylamine gives 2 - methyl - 3 - hydroxy-3-cyclopropyl-1-isoindolinone ( 4b), which is converted by hydrogen halides in chloroform to the rearranged homoallylic halides 5a–c. Thionyl chloride in chloroform converts 2 to 3-(3-chloropropylidene) phthalide ( 7) which upon reaction with methylamine gives isoshihunine ( 8). Heating of keto acid 2 with aniline leads to N-phenyl-N-norshihunine ( 9), while upon heating of 2 with methylamine spiro [(1 - methylpyrrolidine) - 2 - 3′ - (2′ - methyl - 1′ - isoindolinone)] ( 10) is obtained. 10 is converted to shihunine ( 1) by 48% HBr solution. The mechanisms of the reactions are discussed.
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