☆ 4.7 Article

Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene

JOURNAL OF ORGANIC CHEMISTRY (2015)

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

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Chemistry, Organic

资金

Petroleum Research Fund
Zabriskie Fellowship at Dartmouth College

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摘要

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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