Synthesis of gamma- and delta-lactones from 1alpha-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

Agnieszka Wojtkielewicz; Jacek W Morzycki

doi:10.1016/j.steroids.2007.03.005

Synthesis of gamma- and delta-lactones from 1alpha-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

Steroids. 2007 Jun;72(6-7):552-8. doi: 10.1016/j.steroids.2007.03.005. Epub 2007 Mar 18.

Authors

Agnieszka Wojtkielewicz¹, Jacek W Morzycki

Affiliation

¹ Institute of Chemistry, University of Bialystok, Al. Pilsudskiego 11/4, 15-443 Bialystok, Poland.

PMID: 17493648
DOI: 10.1016/j.steroids.2007.03.005

Abstract

New synthetic pathway towards 19-functionalized derivatives of 1alpha-hydroxy-5,6-trans-vitamin D3 was described. Ring-closing metathesis (RCM) of 1alpha-hydroxy-5,6-trans-vitamin D3 1-omega-alkenoates was a key-step. Hydride reduction of resulting lactones led to the new vitamin D3 analogues.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Hydroxycholecalciferols / chemistry*
Lactones / chemical synthesis*
Magnetic Resonance Spectroscopy
Metals / chemistry*
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared

Substances

Hydroxycholecalciferols
Lactones
Metals