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)]


Published in:
Chemistry--A European Journal, 11, 9, 2668-2679
Year:
2005
Keywords:
Note:
CAN 143:97554
31-6
Alkaloids
Institut de Chimie des Substances Naturelles CNRS,Gif-sur-Yvette,Fr.
Journal
0947-6539
written in English.
38478-72-7P (Mauritine A); 38478-73-8P (Mauritine B); 54578-03-9P (Mauritine C); 55609-23-9P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (total synthesis and NMR assignment of mauritines A, B, C, and F); 2439-38-5; 2812-31-9; 13734-34-4; 13734-41-3; 45170-31-8; 204264-63-1; 204264-64-2; 312583-31-6 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of mauritines A, B, C, and F via nucleophilic arom. substitution); 312583-22-5P; 312583-23-6P; 312583-24-7P; 312583-25-8P; 313055-04-8P; 313055-05-9P; 856165-42-9P; 856165-43-0P; 856165-44-1P; 856165-45-2P; 856165-46-3P; 856165-47-4P; 856165-48-5P; 856165-49-6P; 856165-50-9P; 856165-51-0P; 856165-52-1P; 856245-57-3P; 856250-62-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of mauritines A, B, C, and F via nucleophilic arom. substitution)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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