Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: a formal asymmetric synthesis of (-)-detoxinine.
We report herein two stereocomplementary approaches to erythro/trans and threo/cis vicinal amino diol subunits containing 2-pyrrolidinones (9 and 10) starting from the known enamides 7, easily available from malimides. The first approach consists of an epoxidation-reductive dehydroxylation procedure, and the second one is based on hydroboration-oxidation reactions. Using the second method, a formal asymmetric synthesis of (-)-detoxinine was achieved.
Zhou
Xiang
X
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, PR China.
Liu
Wen-Jun
WJ
Ye
Jian-Liang
JL
Huang
Pei-Qiang
PQ
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006900:Hydroxylation; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D011759:Pyrrolidines; D011760:Pyrrolidinones; C525416:detoxinine; C028537:2-pyrrolidone