A concise enantioselective synthesis of a key A-ring synthon for 1 alpha-hydroxyvitamin D-3 compounds

Authors
Hiyamizu, H Ooi, H Inomoto, Y Esumi, T Iwabuchi, Y Hatakeyama, S
Citation
H. Hiyamizu et al., A concise enantioselective synthesis of a key A-ring synthon for 1 alpha-hydroxyvitamin D-3 compounds, ORG LETT, 3(3), 2001, pp. 473-475
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
473 - 475
Database
ISI
SICI code
1523-7060(20010208)3:3<473:ACESOA>2.0.ZU;2-A
Abstract
[GRAPHICS] This report describes a concise enantioselective synthesis of the A-ring sy nthon for the synthesis of 1 alpha -hydroxyvitamin D-3 compounds, The synth esis involves two notable transformations: (i) stereoselective construction of the enol triflate from the vinyl ketone by Michael addition of Ph2P(O)L i followed by in situ triflation of the resulting enolate and (ii) palladli um catalyzed Heck type cyclization of the enol triflate.