Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis |
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| Institution: | 1. Universidade Federal do Rio de Janeiro, Instituto de Ciências Biomédicas, Laboratório de Farmacologia da Dor e da Inflamação, Av. Carlos Chagas Filho, 373. Prédio do CCS, bloco J, sala 10, 21941-902 Rio de Janeiro, Brazil;2. Universidade Federal do Rio de Janeiro, Instituto de Química, Rio de Janeiro, Brazil |
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| Abstract: | The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed π-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography. |
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