First Syntheses of Lorneic Acids A and B with Potential PDE5 Inhibition Activity

Two natural products with potential PDE5 inhibition activity, lorneic acids A and B, have been synthesized for the first time in high yield using a chiral amide stereocontrolled addition of aryl lithium to aldehyde as the key step, and the configuration of the chiral benzylic alcohol in lorneic acid...

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Bibliographic Details
Published inSynlett no. 4; pp. 607 - 610
Main Authors Ma, Xiang, Song, Yuting, Liu, Hao, Chen, Ruijiao, Chen, Xiaochuan
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
hiral auxiliary
ortho-lithiation
METALATION
asymmetric synthesis
BENZAMIDES
ASYMMETRIC INDUCTION
SECONDARY
lorneic acid A/B
PDE5 inhibitor
CYCLIZATION
AMIDES
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Summary:Two natural products with potential PDE5 inhibition activity, lorneic acids A and B, have been synthesized for the first time in high yield using a chiral amide stereocontrolled addition of aryl lithium to aldehyde as the key step, and the configuration of the chiral benzylic alcohol in lorneic acid B was determined to be S.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290352