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Synthesis of (−)‐Neplanocin A from ( R,R )‐Tartaric Acid
Author(s) -
Bestmann Hans Jürgen,
Roth Dieter
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199000991
Subject(s) - cyclopentenone , tartaric acid , stereochemistry , chemistry , combinatorial chemistry , organic chemistry , citric acid
The synthesis of the carbocyclic nuclcoside analogue 1 from ( R,R )‐tartaric acid involves eleven steps via intermediary formation of the cyclopentenone 2 . Since organolithium compounds other than LiGH 2 OCH 2 OCH 3 can also be added to 2 , any desirable 3‐substituted derivatives of 1 are, in principle, accessible in this way. (−)‐Neplanocin A is of special importance since it exhibits both antiviral as well as antitumor activity.
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