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

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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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 11; pp. 1043 - 1044
Main Authors Chida, N, Yoshinaga, M, Tobe, T, Ogawa, S
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1997
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
TRIACETOXYBOROHYDRIDE
NK10958
OLEFINATION
REAGENTS
REDUCTION
DERIVATIVES
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/a701404j