Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D3

Autor:	Katelyn B. Connell, Elizabeth A. Dethoff, Varun Mehta, William H. Miles, April J Thrall, Gözde Ulas, Hannah H. Tuson
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Ketone Molecular Structure Calcitriol Stereochemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Chemical synthesis chemistry.chemical_compound chemistry Furan medicine Furans Ene reaction Lactone Peterson olefination medicine.drug
Zdroj:	The Journal of Organic Chemistry. 75:6820-6829
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo101155c
Popis:	The A-rings of calcitriol (1α,25-dihydroxyvitamin D(3)) and 1α-hydroxy-3-deoxyvitamin D(3) were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel-Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fe38d8d53df278a8055c98d89b7a1626 https://doi.org/10.1021/jo101155c Zobrazit plný text záznamu