13-Step
Total Synthesis of Atropurpuran
Shengling Xie
Gui Chen
Hao Yan
Jieping Hou
Yongping He
Tongyun Zhao
Jing Xu
10.1021/jacs.9b00391.s001
https://acs.figshare.com/articles/journal_contribution/13-Step_Total_Synthesis_of_Atropurpuran/7732598
Herein, we report
a concise total synthesis of atropurpuran, a
unique and synthetically challenging pentacyclic diterpene that bears
a tetracyclo[5.3.3.0<sup>4,9</sup>.0<sup>4,12</sup>]-tridecane skeleton
that is unprecedented among natural terpenes. This 13-step approach
features a strategy that include early stage rapid skeleton formation
and the late-stage introduction of reactive functional groups, thus
allowed a high overall synthetic efficiency with minimal use of PGs.
The key transformations of our work include a facile construction
of the spiro[5.5]undecane moiety through an ring-closing enyne metathesis
reaction and an efficient formation of the tetracyclo[5.3.3.0<sup>4,9</sup>.0<sup>4,12</sup>]-tridecane scaffold via an regioselective
double oxidative dearomatization/intramolecular Diels–Alder
reaction cascade. This efficient approach should also inspire further
advances in the synthesis of related complex diterpenes and diterpenoid
alkaloids.
2019-02-13 00:00:00
ring-closing enyne metathesis reaction
tetracyclo
oxidative
dearomatization
cascade
diterpenoid alkaloids
moiety
tridecane
PG
spiro
Atropurpuran Herein
synthetically
late-stage introduction
strategy
reactive
atropurpuran
skeleton formation
scaffold
.0
advance
pentacyclic diterpene
transformation
synthesis
Diel
efficiency
13- step approach features
regioselective
13- Step
construction
Synthesi