Total synthesis of (-)-PA-48153C (pironetin) utilising l-quebrachitol as a chiral building block

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Noritaka Chida, Mitsukane Yoshinaga, Takahiko Tobe and Seiichiro Ogawa


Abstract

The chiral and stereoselective synthesis of (-)-PA-48153C (pironetin) 1, a novel immunosuppressant, is described; the acyclic portion possessing four contiguous chiral centres in 1 was constructed stereoselectively from L-quebrachitol and the 2-pyranone moiety was prepared from L-malic acid.


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