Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine.
The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel--Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.
Wipf
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Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu
Hopkins
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D000478:Alkylation; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007202:Indicators and Reagents; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D010880:Piperidines; C069637:tetrazomine