Total Synthesis of Ansellone G and Phorbadione.

J Org Chem

Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.

Published: December 2022

AI Article Synopsis

  • The total synthesis of marine sesterterpenoid ansellone G was achieved using Prins cyclization of a chloro-substituted homoallyl alcohol to create a hydrobenzopyran structure.
  • Chloro groups were preintroduced to assist in transforming functional groups after building the carbon framework.
  • Phorbadione was also synthesized through dehydration of a tertiary alcohol, and the synthesized compounds were tested for their HIV latency-reversing activity.

Article Abstract

The first total synthesis of marine sesterterpenoid ansellone G () was accomplished. This strategy utilizes the Prins cyclization reaction of a chloro-substituted homoallyl alcohol to synthesize the hydrobenzopyran skeleton. The preintroduction of the chloro groups facilitated the functional group transformation for after constructing the carbon framework. Furthermore, we also successfully synthesized phorbadione () by dehydrating the tertiary alcohol. The HIV latency-reversing activity of the synthesized , , and deacetylated was also evaluated.

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Source
http://dx.doi.org/10.1021/acs.joc.2c02278DOI Listing

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