期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2017, 期 20, 页码 2883-2915出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700195
关键词
Arynes; Asymmetric dihydroxylation; Diels-Alder addition; Naphthalenes; Natural products; Cyclization
3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels-Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-gamma-lactones. This occurred by a succession of (1) Heck coupling, (2) asymmetric dihydroxylation, (3) oxa-Pictet-Spengler cyclization, and (4) oxidation. The fifteen monomeric naphthoquinonopyrano-gamma-lactone structures that we prepared resemble the natural product (-)-arizonin C1 or its C-5 epimer. Accordingly, they represent hexasubstituted naphthalenes likewise. The sixteenth naphthoquinonopyrano-gamma-lactone that we synthesized is a kind of dimer. Its moieties are bridged differently than those in naturally occurring naphthoquinonopyrano-gamma-lactone dimers.
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