An Enantioconvergent Synthesis of (R)-4-Aryloxy-1-butyne-3-ols for Prostanoid Side Chains
2002; Wiley; Volume: 344; Issue: 1 Linguagem: Inglês
10.1002/1615-4169(200201)344
ISSN1615-4169
AutoresMartin E. Fox, Mark Jackson, Ian C. Lennon, Raymond McCague, Julian S. Parratt,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe 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.
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