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

Anupama Kumari, Sachin P. Gholap, Rodney A. Fernandes^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2278-2290
Number of pages	13
Journal	Chemistry - An Asian Journal
Volume	14
Issue number	13
DOIs	https://doi.org/10.1002/asia.201900421
State	Published - 1 Jul 2019
Externally published	Yes

Keywords

coriolides
enal
guggultetrol
oxidation
tandem reaction

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10.1002/asia.201900421

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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",

author = "Anupama Kumari and Gholap, {Sachin P.} and Fernandes, {Rodney A.}",

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doi = "10.1002/asia.201900421",

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AU - Kumari, Anupama

AU - Gholap, Sachin P.

AU - Fernandes, Rodney A.

PY - 2019/7/1

Y1 - 2019/7/1

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AB - 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.

KW - coriolides

KW - enal

KW - guggultetrol

KW - oxidation

KW - tandem reaction

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SN - 1861-4728

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ER -

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

Abstract

Keywords

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