Organic Letters, volume 3, issue 3, pages 473-475
A Concise Enantioselective Synthesis of a Key A-Ring Synthon for 1α-Hydroxyvitamin D3 Compounds
Hiroko HIYAMIZU
1
,
Hidenori OOI
1
,
Yoko Inomoto
1
,
Tomoyuki Esumi
1
,
Yoshiharu Iwabuchi
1
,
Susumi Hatakeyama
1
Publication type: Journal Article
Publication date: 2001-01-12
Journal:
Organic Letters
scimago Q1
wos Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
11428042
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
[figure: see text] This report describes a concise enantioselective synthesis of the A-ring synthon for the synthesis of 1 alpha-hydroxyvitamin D3 compounds. The synthesis involves two notable transformations: (I) stereoselective construction of the enol triflate from the vinyl ketone by Michael addition of Ph2P(O)Li followed by in situ triflation of the resulting enolate and (II) palladium-catalyzed Heck type cyclization of the enol triflate.
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