title: Asymmetric synthesis of (+)-pyrido[3,4-b]homotropane.
abstract: (+)-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.
authors.affiliation: Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Sang
authors.forename: Jingrui
authors.initials: J
authors.lastname: Zhao
authors.forename: Xueshun
authors.initials: X
authors.lastname: Jia
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
mesh_terms: D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011725:Pyridines; D014326:Tropanes; C055134:pyrido(3,4-b)norhomotropane