Journal
TETRAHEDRON
Volume 68, Issue 16, Pages 3283-3287Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.03.007
Keywords
Dizocilpine; Dibenzosuberenone; Aziridination; Hydrogenolysis; BF3 center dot OEt2-promoted cyclization; Desulfonylation
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Funding
- National Science Council of the Republic of China [NSC 99-2113-M-037-006-MY3]
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A simple five-step synthetic route toward dizocilpine (1) starting with dibenzosuberenone (2) in 28% of total yield is described. The facile route was carried from by aziridination of dibenzosuberenone (2) with NBS and chloramines-T in MeCN at reflux, hydrogenolysis of azridinyl ketone, Grignard methylation of amino ketone, BF3 center dot OEt2-promoted cyclization of amino alcohol, and desulfonylation with Mg and Et3N in MeOH. Anthracene skeleton 9 is also synthesized via an intramolecular rearrangement of pinacol to pinacolone. (C) 2012 Elsevier Ltd. All rights reserved.
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