Synthesis of C-19-functionalized 1alpha-hydroxyvitamin D(2) analogues via ring-closing metathesis.
A heteroatom-tethered regioselective ring-closing metathesis reaction was used for the C-19 functionalization of 1alpha-hydroxy-5,6-trans-vitamin D(2) analogues. Applications of the reaction to form a range of analogues by manipulation of the tether using both organolithium reagents and Diels-Alder cycloadditions are described.
Ahmed
Mahmood
M
Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.
Atkinson
Catherine E
CE
Barrett
Anthony G M
AG
Malagu
Karine
K
Procopiou
Panayiotis A
PA
D003500:Cyclization; D004872:Ergocalciferols / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D008665:Metalloporphyrins / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc
D004872:Ergocalciferols; D007202:Indicators and Reagents; D008665:Metalloporphyrins; C042533:1 alpha-hydroxyergocalciferol; D015032:Zinc