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Stereoselective convergent synthesis of a trans-fused polycyclic ether ring system including a
Keisuke Suzuki1, Tadashi Nakata
1Graduate School of Science and Engineering, Saitama University, Japan.
Organic Letters
|August 3, 2002
Abstract:
[reaction: see text] Stereoselective convergent synthesis of a trans-fused 6-6-6-6-membered tetracyclic ether ring system including 4alpha- or 4beta-hydroxy-5-methyl-tetrahydropyran was achieved. The key reactions involve the acetylide-aldehyde coupling of two tetrahydropyrans, intramolecular hetero-Michael cyclization of enone, stereoselective reduction of enone, hydroboration, intramolecular acetalization, and stereoselective reduction of the acetal with Et(3)SiH-TMSOTf.