ol7b00722_si_001.pdf (4.9 MB)
Total Synthesis of Scholarisine K and Alstolactine A
journal contribution
posted on 2017-03-30, 16:20 authored by Dan Wang, Min Hou, Yue Ji, Shuanhu GaoThe 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.