The 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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