Conformationally constrained analogues of diacylglycerol. 24. Asymmetric synthesis of a chiral (R)-DAG-lactone template as a versatile precursor for highly functionalized DAG-lactones

Organic Letters
Ji-Hye KangVictor E Marquez

Abstract

[structure: see text] Commercially available 2-methylenepropane-1,3-diol was converted to chiral epoxide (R)-2 via Sharpless asymmetric epoxidation in >96% ee. Regiospecific epoxide ring opening and reduction of the intermediate alkyne set the stage for a one-pot lactonization to give (R)-6, a convenient precursor for all functionalized chiral DAG-lactones used as potent PK-C ligands. The synthesis of the most potent DAG-lactones known to date, (Z)-10 and (E)-10, served to confirm PK-C's exclusive preference for the (R)-stereochemistry in this class of compounds.

References

Jun 18, 2003·Accounts of Chemical Research·Victor E Marquez, Peter M Blumberg

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Citations

Nov 13, 2012·Biotechnology Advances·Vipin Chandra Kalia
Aug 6, 2016·The Journal of Organic Chemistry·David O BaumannGary E Keck
May 20, 2017·Pharmaceuticals·Marta RuiSimona Collina
Nov 22, 2005·Bioorganic & Medicinal Chemistry·Jeewoo LeePeter M Blumberg
Apr 23, 2013·Chemistry : a European Journal·Max Bielitza, Jörg Pietruszka
Sep 11, 2012·Organic & Biomolecular Chemistry·Aurélien TapJanick Ardisson
Oct 11, 2014·Organic & Biomolecular Chemistry·Mark BetsonPhilip Wainwright
Nov 23, 2010·Chemical Reviews·Neri AmaraMichael M Meijler

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