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Synfacts 2018; 14(08): 0777
DOI: 10.1055/s-0037-1609882
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Hosieine A

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Huang Y.-W. Kong K. Wood JL. * Baylor University, Waco, USA
Total Synthesis of (+)- and (±)-Hosieine A.

Angew. Chem. Int. Ed. 2018;
57: 7664-7667
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Further Information

Publication History

Publication Date:
18 July 2018 (online)

 
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Key words

(+)-hosieine A - Rautenstrauch rearrangement - enantioconvergent gold catalysis - Michael addition

Significance

The authors report a nine-step total synthesis of enantioenriched (+)-hosieine A. Natural products of the hosieine family were isolated from O. hosiei and show nanomolar activity against the nicotinic acetylcholine receptors ­(nAChRs). For a previous synthesis of (–)-hosieine A, see: J. Ouyang, R. Yan, X. Mi, R. Hong Angew. Chem. Int. Ed. 2015, 54, 10940.


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Comment

The synthesis relied on a gold- catalyzed, enantioconvergent Rautenstrauch rearrangement that afforded enone K. After base- induced Michael addition to form L and reductive amination, spontaneous lactamization took place to give N. The lactam was reduced eventually with borane to give enantioenriched (+)-hosieine A.


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