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An Enantioconvergent Synthesis of ( R )‐4‐Aryloxy‐1‐butyne‐3‐ols for Prostanoid Side Chains
Author(s) -
Fox Martin E.,
Jackson Mark,
Len Ian C.,
McCague Raymond,
Parratt Julian S.
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200201)344:1<50::aid-adsc50>3.0.co;2-5
Subject(s) - chemistry , alcohol , acylation , side chain , enantiomer , carboxylate , organic chemistry , mesylate , stereochemistry , catalysis , polymer
The single enantiomer title alcohols, useful as ω‐side chain precursors for pharmaceutically important prostaglandin analogues were synthesised from the corresponding racemic alcohols by a convenient 4‐step sequence. After enzymatic acylation of the alcohol with a vinyl carboxylate, the residual ( S )‐alcohol in the mixture was converted to the mesylate. Subsequent displacement with the corresponding carboxylate anion, followed by enzymatic deacylation gave the desired ( R )‐alcohol. In this way, all of the starting alcohol was utilised without the need for separation of the starting material and product after the bioresolution.