Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block |
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| Authors: | Shimizu Masato Iwasaki Yukiko Shibamoto Yoshinori Sato Miki DeLuca H F Yamada Sachiko |
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| Institution: | Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kandasurugadai, Chiyoda-ku, Tokyo 101-0062, Japan. shimizu.mr@tmd.ac.jp |
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| Abstract: | 19-norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method. |
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