First Total Syntheses of Oresbiusins A and B, Their Antipodes, and Racemates: Configuration Revision and Anti-HIV Activity

[摘要]：The first total syntheses of oresbiusin A in the (+)-, ()-, and (+/-)-forms were accomplished in five steps with overall yields of ca. 70?%. The key intermediates with optical activity were generated through a Sharpless asymmetric dihydroxylation reaction. These efforts allowed us to establish the absolute configuration of this natural product with dextrorotary and a 2S configuration. In addition, the total syntheses of both enantiomers of oresbiusin B along with its racemate were accomplished in six steps with overall yields of 58?%. Among these compounds, the unnatural oresbiusin A with a levorotary rotation was found to possess dose dependent anti-HIV-1 activity in H9 cells, whereas the other compounds were inactive.

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