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A Short Total Synthesis of Kuehneromycin A
Author(s) -
Jauch Johann
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000804)39:15<2764::aid-anie2764>3.0.co;2-s
Subject(s) - intramolecular force , key (lock) , chemistry , protocol (science) , reverse transcriptase , combinatorial chemistry , total synthesis , stereochemistry , computer science , biochemistry , rna , medicine , computer security , alternative medicine , pathology , gene
Only eleven steps were needed to synthesize kuehneromycin A ( 1 ) which inhibits reverse transcriptase (see picture). Key steps are a new variant of the Baylis–Hillman reaction, an endo ‐selective intramolecular Diels–Alder reaction, and a new protocol for the Parikh–Doering oxidation. TBDPS= tert ‐butyldiphenylsilyl.