Section 12
Chapter 11,074

Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block

Shimizu, M.; Iwasaki, Y.; Shibamoto, Y.; Sato, M.; Deluca, H.F.; Yamada, S.

Bioorganic and Medicinal Chemistry Letters 13(5): 809-812


ISSN/ISBN: 0960-894X
PMID: 12617896
DOI: 10.1002/chin.200330235
Accession: 011073587

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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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