Enantioselective Synthesis of the AB-Ring System of the Antitumor Antibiotic Tetrazomine
- 28 March 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (9) , 3133-3139
- https://doi.org/10.1021/jo015512q
Abstract
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.Keywords
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