期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 21, 页码 11189-11192出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01972
关键词
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资金
- Petroleum Research Fund
- Zabriskie Fellowship at Dartmouth College
A new synthesis of dibenzo[a,c]anthracene (4) is described that features the generation, from tetrabromo-bis-triflate 1 and phenyllithium, of a 1,3,6-naphthotriyne (2) synthetic equivalent that is trapped with 3 equiv of furan to form Diels-Alder tris-adduct 3. A subsequent two-step deoxygenation of 3 represents the first synthesis of dibenz[a,c]anthracene (4) that involves a tandem aryne Diels-Alder cycloaddition-deoxygenation strategy.
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