TY - JOUR
T1 - Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis
AU - CRAVOTTO, G
AU - GIOVENZANA, Giovanni Battista
AU - PALMISANO, G
AU - PENONI, A
AU - PILATI, T
AU - SISTI, M
AU - STAZI, F.
N1 - Funding Information:
Financial support from Regione Piemonte (Ricerca Scientifica Applicata 2004) is gratefully acknowledged.
PY - 2006
Y1 - 2006
N2 - 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.
AB - 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.
UR - https://iris.uniupo.it/handle/11579/19362
U2 - 10.1016/j.tetasy.2006.11.021
DO - 10.1016/j.tetasy.2006.11.021
M3 - Article
SN - 0957-4166
VL - 17
SP - 3070
EP - 3074
JO - TETRAHEDRON-ASYMMETRY
JF - TETRAHEDRON-ASYMMETRY
IS - 22
ER -