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

• Published in: The Journal of steroid biochemistry and molecular biology Vol. 173; pp. 86 - 88
• Main Authors: Sigüeiro, Rita, Otero, Rocio, González-Berdullas, Patricia, Loureiro, Julian, Mouriño, Antonio, Maestro, Miguel A.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.10.2017
• Subjects: 19-Nor-A-ring phosphine oxide; 19-Nor-calcitriol; Calcitriol - analogs & derivatives; Calcitriol - chemical synthesis; Chemistry Techniques, Synthetic - methods; Convergent synthesis; Monoterpenes - chemical synthesis; Monoterpenes - chemistry; Oxides - chemical synthesis; Oxides - chemistry; Phosphines - chemical synthesis; Phosphines - chemistry; Vitamin D3 metabolites; Vitamins - chemical synthesis; Vitamins - chemistry; Vitamin D3 metabolites; 19-Nor-A-ring phosphine oxide; 19-Nor-calcitriol; Convergent synthesis; Vitamin D metabolites
• ISSN: 0960-0760; 1879-1220
• DOI: 10.1016/j.jsbmb.2016.08.008

•An efficient synthesis of 19-nor-A-ring phospine oxide (5) was achieved from (S)-carvone (7%, 15 steps).•A convergent synthesis of 1α,25-dihydroxy-19-norvitamin D3 (3) was achieved from (S)-carvone and Inhoffen-Lythgoe diol (20 steps, 3%).•The triene system assembly is based on a Wittig-Horner coupling. [Display omitted] 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.