Premium
Tandem IBX‐Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ‐Diolcarbonate Aldehydes to ( E )‐γ‐Hydroxy‐α,β‐enals
Author(s) -
Kumari Anupama,
Gholap Sachin P.,
Fernandes Rodney A.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900421
Subject(s) - aldehyde , tandem , primary (astronomy) , alcohol , chemistry , stereoselectivity , alcohol oxidation , olefin fiber , primary alcohol , organic chemistry , catalysis , materials science , physics , astronomy , composite material
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.