Issue 6, 2015

Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

Abstract

An efficient and asymmetric synthetic approach towards one of the biologically interesting 4(S)-11-diHDHA derivatives was developed. This process mainly relied on two reactions, one is the copper-catalyzed mild cross-coupling that allows for the efficient construction of a chiral α-alkynyl α-hydroxy motif and another is the synthesis of chiral α-hydroxy α-stannanes that has previously been developed by our group featuring the asymmetric stannylation using the well-established tributyltin hydride/diethyl zinc system from an aldehyde.

Graphical abstract: Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
31 Oct 2014
Accepted
12 Nov 2014
First published
13 Nov 2014

Org. Biomol. Chem., 2015,13, 1624-1628

Author version available

Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

R. Wang and J. R. Falck, Org. Biomol. Chem., 2015, 13, 1624 DOI: 10.1039/C4OB02324B

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