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Stereoselective Total Synthesis of (−)-(2S,4R)‑3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
journal contribution
posted on 2020-02-21, 23:43 authored by Ranganayakulu Sunnapu, Saikumar Naik Banoth, Reyno R. S., Aleena Thomas, Navyasree Venugopal, Goreti RajendarThe first stereoselective total synthesis
of (−)-(2S,4R)-3′-methoxy
citreochlorol and
(−)-(2S,4S)-3′-methoxy
citreochlorol is demonstrated. A proline-based imidazolidinone was
synthesized and used as chiral auxiliary for asymmetric acetate aldol
reaction to generate initial chirality in the targeted molecule. Geminal
dichloromethane functionality was introduced by the addition of in
situ generated dichloromethyllithium to Weinreb’s amide functional
group.
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Weinrebstereoselectiveproline-based imidazolidinonedichloromethyllithiumchiralityGeminal dichloromethane functionalitysynthesismethoxymoleculeNew Proline-Based AuxiliaryAsymmetric Acetate Aldol Reactionacetate aldol reactionCitreochlorolMethoxylPreparationchiralamideStereoselectiveSynthesicitreochlorol
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