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Synlett 1999; 1999(12): 1899-1902
DOI: 10.1055/s-1999-2989
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BINOL-Ti-Catalyzed Carbonyl-Ene Cyclization by Tuning the 6-Br-Ligand for the Synthesis of 2-Methyl-19-nor-22-oxa Vitamin D Analogue with Significant Differentiation Activity

Koichi Mikami* , Yurika Koizumi, Ayako Osawa, Masahiro Terada, Hiroaki Takayama, Kimie Nakagawa, Toshio Okano
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan; Fax + 81-3-57 34-27 76; E-mail: kmikami@o.cc.titech.ac.jp
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Publikationsdatum:
31. Dezember 1999 (online)

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Transition state control in BINOL-Ti-catalyzed asymmetric carbonyl-ene cyclization by tuning the 6-Br-BINOL ligand completes the synthesis of the A ring of the 2-methyl-19-nor-22-oxa D3 analogue (2), which shows the significant activity in differentiation of HL-60 cell.

vitamin D - ene reaction - binaphthol - titanium complex - asymmetric catalysis