Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals

Anupama Kumari; Sachin P Gholap; Rodney A Fernandes

doi:10.1002/asia.201900421

Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals

Chem Asian J. 2019 Jul 1;14(13):2278-2290. doi: 10.1002/asia.201900421. Epub 2019 Jun 3.

Authors

Anupama Kumari¹, Sachin P Gholap¹, Rodney A Fernandes¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai Mumbai, 400076, Maharashtra, India.

PMID: 31062934
DOI: 10.1002/asia.201900421

Abstract

A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.

Keywords: coriolides; enal; guggultetrol; oxidation; tandem reaction.

Grants and funding

EMR/2017/000499/Science and Engineering Research Board