Synthesis of (–)-Epicoccin G and (–)-Rostratin A
Efficient and Divergent Total Synthesis of (–)-Epicoccin G and (–)-Rostratin A Enabled by Double C(sp3)–H Activation.
J. Am. Chem. Soc. 2019;
18. November 2019 (online)
Key words(–)-epicoccin G - (–)-rostratin A - dithiodiketopiperazines - C(sp3)–H activation - asymmetric nucleophilic epoxidation
(–)-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.
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.