Enantioselective total synthesis of (-)-monic acid C via carbosulfenylation of a dihydropyran

JD White, P Theramongkol, C Kuroda…

文献索引：White, James D.; Theramongkol, Parinya; Kuroda, Chiaki; Engebrecht, Jeffrey R. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 25  p. 5909 - 5921

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被引用次数: 31

摘要

A stereoselective synthesis of (-)-monic acid C (5) was accomplished in a linear sequence of 22 steps beginning from dihydropyran and with (-)-1-borneol as a chiral auxiliary. 2-(l- Bornyloxy) pyrans 10 and 11 were converted via trans epoxides 12 and 13 to hydroxy selenides 16 and 17. Selenide 16 was transformed to vinyl ether 20, which underwent Claisen rearrangement to 22. The latter, after oxidation to carboxylic acid 24, was treated ...