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A benzyne-insertion approach to hetisine-type diterpenoid alkaloids: synthesis of cossonidine (davisine)

Kou, Kevin G. M., Pflueger, Jason J, Kiho, Toshihiro, Morrill, Louis C., Fisher, Ethan L., Clagg, Kyle, Lebold, Terry P, Kisunzu, Jessica K and Sarpong, Richmond 2018. A benzyne-insertion approach to hetisine-type diterpenoid alkaloids: synthesis of cossonidine (davisine). Journal of the American Chemical Society 140 (26) , pp. 8105-8109. 10.1021/jacs.8b05043

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Abstract

The hetisine-type natural products exhibit one of the most complex carbon skeletons within the diterpenoid alkaloid family. The use of network analysis has enabled a synthesis strategy to access alkaloids in this class with hydroxylation on the A-ring. Key transformations include a benzyne acyl-alkylation to construct a key fused 6-7-6 tricycle, a chemoselective nitrile reduction, and sequential C–N bond formations using a reductive cyclization and a photochemical hydroamination to construct an embedded azabicycle. Our strategy should enable access to myriad natural and unnatural products within the hetisine-type.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Date of First Compliant Deposit: 18 June 2018
Date of Acceptance: 11 June 2018
Last Modified: 05 Feb 2020 15:45
URI: http://orca.cf.ac.uk/id/eprint/112528

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