Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 23, Pages 9202-9206Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b04702
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Funding
- National Science Foundation [CHE-1564340]
- National Institutes of Health [GM-129264]
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Haterumaimide J (hatJ) is reportedly the most cytotoxic member of the lissoclimide family of labdane diterpenoids. The unusual functional group arrangement of hatJ-C18 oxygenation and C2 chlorination resisted our efforts at synthesis until we adopted an approach based on rarely studied terminal epoxide-based cation-pi bicyclizations that is described herein. Using the C2-chlorine atom as a key stereocontrol element and a furan as a nucleophilic terminator, the key structural features of hatJ were rapidly constructed. The 18-step stereoselective synthesis features applications of chiral pool starting materials, and catalyst-, substrate-, and auxiliary-based stereocontrol. Access to hatJ and its acetylated congener hatK permitted their biological evaluation against aggressive human cancer cell lines.
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