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Synthesis of (±)‐Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction
Author(s) -
Pasfield Luke A.,
de la Cruz Laura,
Ho Junming,
Coote Michelle L.,
Otting Gottfried,
McLeod Malcolm D.
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200171
Subject(s) - chemistry , diels–alder reaction , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
Under pressure: Panduratin A ( 1 ) has been synthesized in six steps including a high pressure Diels–Alder reaction. This divergent sequence also allowed the synthesis of 4‐hydroxypanduratin A, panduratin H, panduratin I, nicolaioidesin B, and 2‐hydroxyisopanduratin A. The binding of panduratin A to the dengue virus NS2B‐NS3 protease was investigated by NMR spectroscopy.