Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate ß,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,ß-enals.
Chem Asian J
; 14(13): 2278-2290, 2019 Jul 01.
Article
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| MEDLINE
| ID: mdl-31062934
ABSTRACT
A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate ß,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,ß-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.
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MEDLINE
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En
Revista:
Chem Asian J
Año:
2019
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Article
País de afiliación:
India