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Synthesis 1995; 1995(11): 1405-1410
DOI: 10.1055/s-1995-4114
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Construction of Polycyclic Ring Systems Fused to Cyclobutane by Cascade Reactions of Formyl α,β-Unsaturated Esters

Masataka Ihara, Takahiko Taniguchi, Yuji Tokunaga, Keiichiro Fukumoto*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai, 980-77, Japan, Fax +81(22)2176877
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Publication Date:
31 December 2000 (online)

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The intramolecular Michael-aldol reaction of methyl 7-formyloct-2-enoate (8) using iodotrimethylsilane (TMSI) and hexamethyldisilazane (TMS)2NH produced the separable diastereoisomeric mixture of bicyclo[3.2.0]heptanes 9 and 10. Treatment of the α,β-unsaturated ester 19 possessing a formylcyclopropane function under the same reaction conditions caused cyclopropane ring opening-Michael-aldol reaction to give the bicyclo[3.2.0]heptane 22. The filifolone derivative 31 was synthesized starting from 19 via 22.

intramolecular Michael-aldol reaction - cascade reaction - cyclopropane ring opening-Michael-aldol reaction - filifolone