Total Synthesis of Ansellone G and Phorbadione

The first total synthesis of marine sesterterpenoid ansellone G (2) 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...

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Published in:Journal of organic chemistry 2022-12, Vol.87 (24), p.16913-16917
Main Authors: Yanagihara, Mizushi, Nakahara, Kanae, Kishimoto, Naoki, Abe, Towa, Miura, Satoshi, Misumi, Shogo, Sako, Makoto, Arisawa, Mitsuhiro, Murai, Kenichi
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Language:English
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Alcohols
Cyclization
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cited_by cdi_FETCH-LOGICAL-a329t-5b51f3d8872a7a0926b33ff4be489a63b697b021e281ace8d3fbbf86de95eb553
cites cdi_FETCH-LOGICAL-a329t-5b51f3d8872a7a0926b33ff4be489a63b697b021e281ace8d3fbbf86de95eb553
container_end_page 16917
container_issue 24
container_start_page 16913
container_title Journal of organic chemistry
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creator Yanagihara, Mizushi
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Murai, Kenichi
description The first total synthesis of marine sesterterpenoid ansellone G (2) 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 2 after constructing the carbon framework. Furthermore, we also successfully synthesized phorbadione (3) by dehydrating the tertiary alcohol. The HIV latency-reversing activity of the synthesized 2, 3, and deacetylated 2 was also evaluated.
doi_str_mv 10.1021/acs.joc.2c02278
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subjects Alcohols
Cyclization
title Total Synthesis of Ansellone G and Phorbadione
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