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Synlett 1997; 1997(SI): 451-454
DOI: 10.1055/s-1997-6154
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Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C

Hiroki Sato, Sei-ichi Nakamura, Nobuhide Watanabe, Shun-ichi Hashimoto*
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan, FAX +81(11)706-4981; E-mail hsmt@pharm.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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The total synthesis of zaragozic acid C has been achieved by a convergent strategy, wherein the key feature of the construction of 2,8-dioxabicyclo[3.2.1]octane core structure is a simultaneous creation of the C4 and C5 quaternary carbon centers by Sn(OTf)2-promoted aldol coupling reaction between α-keto ester and silyl ketene thioacetal derived from L- and D-tartaric acids, respectively.

zaragozic acid C - squalene synthase inhibitor - Sn(OTf)2-promoted aldol coupling reaction - silyl ketene thioacetal - α-keto ester