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Total Syntheses of Ningalins D and G

Jang-Yeop Kim¹, Dong-Hyun Kim¹, Tae-Hong Jeon¹

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

Organic Letters

|August 23, 2017

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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