title: Total Synthesis of Scholarisine K and Alstolactine A.
abstract: The first asymmetric total syntheses of scholarisine K and alstolactine A have been accomplished. Our syntheses feature (1) ring closure metathesis and an intramolecular Heck reaction to construct the 1,3-bridged [3,3,1] bicycle (C-D ring), (2) intramolecular alkylation followed by Fischer indolization to form the basic skeleton of akuammilines, and (3) bioinspired, acid-promoted epoxide opening/lactonization to generate the second lactone ring of alstolactine A. These results provide evidence of a biogenetic relationship between scholarisine K and alstolactine A, which should facilitate the preparation of other akuammiline-type natural products and their derivatives for functional studies.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N Zhongshan Road, Shanghai 200062, China.
authors.forename: Dan
authors.initials: D
authors.lastname: Wang
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N Zhongshan Road, Shanghai 200062, China.
authors.forename: Min
authors.initials: M
authors.lastname: Hou
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N Zhongshan Road, Shanghai 200062, China.
authors.forename: Yue
authors.initials: Y
authors.lastname: Ji
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N Zhongshan Road, Shanghai 200062, China.
authors.forename: Shuanhu
authors.identifier: 0000-0001-6919-4577
authors.initials: S
authors.lastname: Gao