title: Total synthesis of (-)-lundurine A and determination of its absolute configuration.
abstract: A 15-step total synthesis of (-)-lundurine A (1) from easily accessible (S)-pyrrolidinone 18 is reported. A Simmons-Smith reaction allows the efficient, simultaneous assembly of the cyclopropyl C ring, the six-membered D ring, the seven-membered E ring, and the quaternary carbon stereocenters at C2 and C7. The absolute configuration of natural (-)-lundurine A was deduced to be 2R,7R,20R based on the stepwise construction of the stereocenters during the total synthesis.
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China).
authors.forename: Shuaijiang
authors.initials: S
authors.lastname: Jin
authors.forename: Jing
authors.initials: J
authors.lastname: Gong
authors.forename: Yong
authors.initials: Y
authors.lastname: Qin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D029062:Apocynaceae / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D011083:Polycyclic Compounds; D011760:Pyrrolidinones; C000597197:lundurine A
keywords: Simmons-Smith reaction; absolute configuration; cyclopropyl ring; lundurine; total synthesis