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Synthesis 2002(14): 1953-1955
DOI: 10.1055/s-2002-34382
DOI: 10.1055/s-2002-34382
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Novel Route to Iridoids: Enantioselective Syntheses of Isoiridomyrmecin and α-Skytanthine
Further Information
Received
14 June 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
Abstract
Enantio- and diastereoselective syntheses of the iridoids (-)-isoiridomyrmecin and (+)-α-skytanthine from a common intermediate (6-bromo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one) were achieved. Key steps in both syntheses are conjugated nucleophilic substitutions (SN2′ anti-reactions) with C1 zinc cyanocuprates.
Key words
enantioselective synthesis - cuprates - natural products - zinc - alkaloids
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References
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9This sequence of reactions was carried out with racemic compounds.
13According to control experiments, phthalimide was formed during the preparation of the organozinc compound.