3 years ago

Total Syntheses of Ningalins D and G

Total Syntheses of Ningalins D and G
Tae-Hong Jeon, Jang-Yeop Kim, Dong-Hyun Kim, Woo-Hyung Kim, Cheon-Gyu Cho
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02372

DOI: 10.1021/acs.orglett.7b02372

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