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A Stereoselective Synthesis of Nonracemic (+)‐Desoxoprosophylline by a Tandem Wittig [2+3]‐Cycloaddition Reaction
Author(s) -
Herdeis Claus,
Telser Joachim
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199906)1999:6<1407::aid-ejoc1407>3.0.co;2-t
Subject(s) - wittig reaction , chemistry , stereoselectivity , cycloaddition , tandem , stereochemistry , ascorbic acid , organic chemistry , combinatorial chemistry , catalysis , materials science , composite material , food science
L‐Ascorbic acid serves as chiral starting material for the synthesis of (+)‐desoxoprosophylline. The synthetic pathway includes the formation of an O ‐protected 5‐azido‐2,3‐dideoxysugar which is subjected to a tandem Wittig [2+3]‐cycloaddition reaction, leading to the heterocyclic core unit of (+)‐prosophylline. Stereoselective hydrogenation and chain elongation yields the desired alkaloid.