A Ring-Closing Enyne Metathesis Approach to Functionalized Semicyclic Dienes: The Total Synthesis of (-)-Tetrangomycin

作者：Moodie Lindon W K; Larsen David S^*

来源：European Journal of Organic Chemistry, 2014, 2014(8): 1684-1694.

DOI：10.1002/ejoc.201301627

• Total synthesis
• Asymmetric synthesis
• Natural products
• Cycloaddition
• Metathesis

The angucycline antibiotic (-)-tetrangomycin was synthesized in 13 steps (11% overall yield) by using a stereoselective Diels-Alder reaction between a naphthoquinone and a semicyclic diene to construct the benz[a]anthraquinone ring system. The diene intermediates were synthesized through a ring-closing enyne metathesis reaction. The tertiary alcohol at C-3 was installed by an asymmetric dihydroxylation reaction. The relative stereochemistry of the dienes was verified by the NMR analyses of the cycloadducts that were obtained from their reaction with N-phenylmaleimide. Selective aromatization of the B ring was achieved under oxidative conditions.

• 出版日期2014-3