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...

Full description

Saved in:
Bibliographic Details
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
Format: Article
Language:English
Subjects:
Alcohols
Cyclization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02278