Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 8, Pages 2667-2680Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100339k
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Funding
- National Institutes of Health [CA-034303]
- National Science Foundation [CHE-0806807]
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A new synthetic strategy for construction of the heptacyclic marine fungal alkaloid (+/-)-communesin F has been devised. Key reactions include an intramolecular Heck cyclization of a tetrasubstituted alkene to generate a tetracyclic enamide bearing one of the quaternary carbon centers (C7) of the alkaloid, an intramolecular reductive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containing the southern aminal, a stereoselective N-Boc-lactam enolate C-allylation to introduce the second quaternary carbon center (CS), and an azide reduction/N-Boc-lactam-opening cascade leading to the northern aminal.
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