Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane.
(+)-pyrido[3,4- b]homotropane (PHT) was efficiently constructed in 12 steps from N, N-diisopropylisonicotinamide. The synthesis features (i) RCM reaction in installing the homotropane skeleton, (ii) Snieckus ortho-lithiation of N, N-diisopropylisonicotinamide followed by acylation, (iii) Myer reduction of bulky tertiary amide to alcohol with LiBH 3NH 2, and (iv) utilization of L-glutamic acid to introduce and establish the requisite stereogenic centers.
Sang
Yingxia
Y
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Zhao
Jingrui
J
Jia
Xueshun
X
Zhai
Hongbin
H
D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
D011725:Pyridines; D014326:Tropanes; C055134:pyrido(3,4-b)norhomotropane