Journal article

Total synthesis of mauritines A, B, C, and F: Cyclopeptide alkaloids with a 14-membered paracyclophane unit

A unified strategy for the synthesis of mauritines A (I), B, C, and F has been developed based on a key intramol. nucleophilic arom. substitution reaction (SNAr) for the formation of the strained 14-membered paracyclophane. It was demonstrated that the outcome of the cycloetherification is independent of the stereochem. of the peptide backbone. On the other hand, dehydration of the secondary benzylic alc., via the phenylselenide intermediate, is configuration dependent. A modified reductive deamination procedure via the diazonium intermediate was developed. A complete assignment of proton and carbon NMR spectroscopy signals for these natural products is reported for the first time. [on SciFinder (R)]


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