Synthesis of More Highly Oxidized Alkyl Citrates via Direct Regio- and Stereoselective Oxidation

NP Rossouw; Z Chen; JM White; MA Rizzacasa

Journal article

Synthesis of More Highly Oxidized Alkyl Citrates via Direct Regio- and Stereoselective Oxidation

NP Rossouw, Z Chen, JM White, MA Rizzacasa

Organic Letters | AMER CHEMICAL SOC | Published : 2023

DOI: 10.1021/acs.orglett.3c03232

Abstract

An approach to more highly oxidized alkyl citrates by direct regio- and stereoselective oxidations is reported. The total synthesis and structural assignment of alkyl citrate L-731-128 are described, and the synthesis of its C4 oxidized congener L-731,127 utilized a regio- and stereoselective enolate oxidation with oxygen gas. A highly stereoselective Rubottom oxidation of a cyclic silylketene acetal then enabled oxidation at C2 to afford the cinatrins C1 and C3

University of Melbourne Researchers

Chen, Zongjia Author

Jonathan White Author

Mark Rizzacasa Author

Related Projects (1)

Lessons From Nature: Late Stage Oxidation in Total Synthesis

Grants

Awarded by University of Melbourne

Funding Acknowledgements

N.P.R. thanks The University of Melbourne for the Research Training Scholarship and Rowden White Scholarship. The authors thank the Australian Research Council Discovery Program for funding and Dr. Christian Gunawan and Tony Duncan (Circa Pty. Ltd.) for the generous gift of (S)-(+)-gamma-(hydroxymethyl)-gamma-butyrolactone.