A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol

Rita Sigüeiro; Rocio Otero; Patricia González-Berdullas; Julian Loureiro; Antonio Mouriño; Miguel A Maestro

doi:10.1016/j.jsbmb.2016.08.008

A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol

J Steroid Biochem Mol Biol. 2017 Oct:173:86-88. doi: 10.1016/j.jsbmb.2016.08.008. Epub 2016 Aug 31.

Authors

Rita Sigüeiro¹, Rocio Otero¹, Patricia González-Berdullas¹, Julian Loureiro¹, Antonio Mouriño¹, Miguel A Maestro²

Affiliations

¹ Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
² Departamento de Química Fundamental, Facultad de Ciencias, Universidad de A Coruña, Campus da Zapateira, s/n, E-15071 A Coruña, Spain. Electronic address: miguel.maestro@udc.es.

PMID: 27592138
DOI: 10.1016/j.jsbmb.2016.08.008

Abstract

A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D₃ analogue 1α,25-dihydroxy-19-norvitamin D₃ (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling.

Keywords: 19-Nor-A-ring phosphine oxide; 19-Nor-calcitriol; Convergent synthesis; Vitamin D(3) metabolites.

MeSH terms

Calcitriol / analogs & derivatives
Calcitriol / chemical synthesis*
Chemistry Techniques, Synthetic / methods*
Cyclohexane Monoterpenes
Monoterpenes / chemical synthesis
Monoterpenes / chemistry
Oxides / chemical synthesis
Oxides / chemistry
Phosphines / chemical synthesis
Phosphines / chemistry*
Vitamins / chemical synthesis*
Vitamins / chemistry

Substances

Cyclohexane Monoterpenes
Monoterpenes
Oxides
Phosphines
Vitamins
carvone
phosphine
Calcitriol