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Synfacts 2019; 15(12): 1341
DOI: 10.1055/s-0039-1691075
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Epicoccin G and (–)-Rostratin A

Contributor(s):
Erick M. Carreira
,
Moritz J. Classen
Thesmar P, Baudoin O. * University of Basel, Switzerland
Efficient and Divergent Total Synthesis of (–)-Epicoccin G and (–)-Rostratin A Enabled by Double C(sp3)–H Activation.

J. Am. Chem. Soc. 2019;
141: 15779-15783
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Further Information

Publication History

Publication Date:
18 November 2019 (online)

 
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Key words

(–)-epicoccin G - (–)-rostratin A - dithiodiketopiperazines - C(sp3)–H activation - asymmetric nucleophilic epoxidation

Significance

(–)-Epicoccin G and (–)-rostratin A are members of the dithiodiketopiperazine family of natural products, whose members exhibit several biological activities, including in vitro anti-HIV-1 activity. The reported synthesis uses a C(sp3)–H activation to construct a common intermediate utilized in the synthesis of both natural products.


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Comment

Asymmetric nucleophilic epoxidation of A followed by vinyl triflate formation afforded intermediate C. C(sp3)–H activation of F led to G, which was subsequently transformed into H, a common precursor for (–)-epicoccin G and (–)-rostratin A.Further insights can also be found in this issue: Synfacts 2019, 15, 1423.


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