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Synlett 2001; 2001(12): 1935-1937
DOI: 10.1055/s-2001-18777
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Total Synthesis of (±)-Smenospondiol by Titanium(III)-Mediated Tandem Radical Cyclization

Yamada Haruo* , Tsuyoshi Hasegawa, Hiroshi Tanaka, Takashi Takahashi
  • *Department of Applied Chemistry, Tokyo Institute of Technology, Ookayama, Meguro, Tokyo 152-8552, Japan; Fax: + 81(3)57342884; E-mail: ttakashi@o.cc.titech.ac.jp
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Publication Date:
04 December 2001 (online)

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We describe the total synthesis of (±)-smenospondiol (1). Stereoselective construction of the drimane skeleton was accomplished by titanium(III)-mediated tandem radical cyclization of epoxide 9. Non-polar solvent is essential for the success of the tandem cyclization.

tandem radical cyclizations - titanium - sesquiterpene hydroquinones - smenospondiol - drimane skeletons