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Org Lett. 2014 Sep 19;16(18):4904-7. doi: 10.1021/ol5024163. Epub 2014 Aug 29.

Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

Author information

1
Tri-Institutional PhD Program in Chemical Biology, Laboratory for Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center , 1275 York Avenue, New York, New York 10065, United States.

Abstract

The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product.

PMID:
25171639
PMCID:
PMC5633934
DOI:
10.1021/ol5024163
[Indexed for MEDLINE]
Free PMC Article

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