Efficient and Divergent Total Synthesis of (-)-Epicoccin G and (-)-Rostratin A Enabled by Double C(sp; 3; )-H Activation

Thesmar, Pierre and Baudoin, Olivier. (2019) Efficient and Divergent Total Synthesis of (-)-Epicoccin G and (-)-Rostratin A Enabled by Double C(sp; 3; )-H Activation. Journal of the American Chemical Society, 141. pp. 15779-15783.

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Official URL: https://edoc.unibas.ch/72153/

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Dithiodiketopiperazines are complex polycyclic natural products possessing a variety of interesting biological activities. Despite their interest, relatively few total syntheses have been completed. We herein report the enantioselective, scalable, and divergent total synthesis of two symmetrical pentacyclic dithiodiketopiperazines, (-)-epicoccin G and (-)-rostratin A. A common intermediate was synthesized on a multigram scale from inexpensive, commercially available starting materials using an enantioselective organocatalytic epoxidation and a double C(sp; 3; )-H activation as key steps, with the latter allowing the efficient simultaneous construction of the two five-membered rings. In addition to the; cis,cis; -fused target (-)-epiccocin G, the more challenging (-)-rostratin A, possessing two; trans; ring junctions, was obtained for the first time on a 500 mg scale through the optimization of each step and validation on multigram quantities. Both natural products were synthesized with high overall yields (13-20%). This study should facilitate access to this fascinating and yet understudied family of biologically active natural products.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:26 Sep 2020 01:30
Deposited On:22 Oct 2019 07:21

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