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Synlett 1990; 1990(11): 691-693
DOI: 10.1055/s-1990-21213
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Enantioselective Preparation of Functionalized Cyclopentanes Using Lewis Acid Mediated Cyclization of Epoxy Allylsilanes: Enantiocontrolled Total Synthesis of (+)-Brefeldin A

Susumi Hatakeyama* , Kazutoshi Sugawara, Mitsuhiro Kawamura, Seiichi Takano
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication Date:
08 March 2002 (online)

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Tin(IV) chloride mediated cyclization of epoxy allylsilanes 2a-c [(2R,3R)-2,3-epoxy-9-trimethylsilyl-7-nonen-1-ols] bearing alkoxy functionalities has been examined establishing an efficient method for the preparation of functionalized chiral cyclopentanes and cyclopentanones. This methodology was utilized in the enantiocontrolled synthesis of (+)-brefeldin A (1,6,7,8,9,11a, 12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent[f]-oxacyclotridecin-4-one) from (R)-(-)-epichlorohydrin.