Stereoselective synthesis of 1ß,25-Dihydroxyvitamin D^sub 3^ and its 26,27-hexadeuterated derivative

A mild convergent synthesis of 1β,25-dihydroxyvitamin D3 (3a), a metabolite of vitamin D3, and its C26,27-hexadeuterated derivative (3b) are described. The A-ring and the CD-fragments are constructed from (R)-carvone and Inhoffen-Lythgoe diol, respectively. The triene system is assembled by a Pd(0)-...

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Published inThe Journal of steroid biochemistry and molecular biology Vol. 164; p. 56
Main Authors Loureiro, Julian, Maestro, Miguel A, Mouriño, Antonio, Sigüeiro, Rita
Format Journal Article
LanguageEnglish
Published Oxford Elsevier BV 01.11.2016
Subjects
Carvone
Chemical synthesis
Metabolites
Vitamin D
Vitamin D3
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Summary:A mild convergent synthesis of 1β,25-dihydroxyvitamin D3 (3a), a metabolite of vitamin D3, and its C26,27-hexadeuterated derivative (3b) are described. The A-ring and the CD-fragments are constructed from (R)-carvone and Inhoffen-Lythgoe diol, respectively. The triene system is assembled by a Pd(0)-catalyzed process, which involves an enol-triflate (A-ring fragment) and an alkenyl boronate (CD-side chain fragment). Deuterium labeling is introduced at the last step of the synthesis.
ISSN:0960-0760
1879-1220