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Org Lett. 2017 Sep 1;19(17):4688-4691. doi: 10.1021/acs.orglett.7b02372. Epub 2017 Aug 22.

Total Syntheses of Ningalins D and G.

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1
Center for New Directions in Organic Synthesis, Department of Chemistry, Hanyang University , 222 Wangshimni-ro, Seongdong-gu, Seoul 04763, Korea.

Abstract

A flexible synthetic strategy for the total syntheses of ningalins D and G is described. The highly effective TMS-OTf/2,6-lutidine-mediated [3,3]-sigmatropic rearrangement of densely loaded dinaphthyl hydrazides and cyclization of the resulting 2,2'-diamino-1,1'-dinaphthyls afforded the key 7H-dibenzo[c,g]carbazole intermediates. Successful conversions to biphenylene quinone methides followed by regioselective brominations completed the total syntheses of the titled marine alkaloids.

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