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Synthetic Approach Towards the Synthesis of Antimalarial Gomphostenin
Author(s) -
Swapnil Nipunge,
Kumar Alleni Suman,
Babu Nanubolu Jagadeesh,
Yadav Jhillu Singh
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700131
Subject(s) - chemistry , stereoselectivity , ketone , wittig reaction , convergent synthesis , stereochemistry , palladium , total synthesis , combinatorial chemistry , catalysis , organic chemistry
An efficient and concise stereoselective synthesis towards the antimalarial (−)‐Gomphostenin, starting with the enantiomerically pure Wieland–Miescher ketone, is reported. The key transformations of the convergent synthesis involved a stereoselective reductive allylation, Palladium‐catalyzed Saegusa–Ito oxidation, Babler–Dauben oxidative rearrangement, and Wittig olefination reactions. The structure and absolute stereochemistry were determined by X‐ray analysis.