ol6b00150_si_002.cif (279.92 kB)
Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C
dataset
posted on 2016-02-29, 16:34 authored by Wang-Bin Sun, Xuan Wang, Bing-Feng Sun, Jian-Ping Zou, Guo-Qiang LinThe
first and asymmetric total synthesis of hedyosumins A, B, and C was
accomplished in 13–14 steps from simple starting materials.
The essential tools that allow us to access the tetracyclic skeleton
include an organocatalytic [4 + 3] cycloaddition reaction, an intramolecular
aldol condensation, and an intramolecular carboxymercuration/demercuration
enabled lactonization. A CBS-catalyzed asymmetric reduction was employed
to boost the ee of the synthetic natural products to an excellent
level. This synthesis established the absolute configurations of hedyosumins
A, B, and C.