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A Concise Total Synthesis of (+)‐Waihoensene Guided by Quaternary Center Analysis
Author(s) -
Peng Cheng,
Arya Piyush,
Zhou Zhiyao,
Snyder Scott A.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004177
Subject(s) - quaternary carbon , alkene , quaternary , total synthesis , chemistry , functional group , center (category theory) , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biology , crystallography , paleontology , polymer
The four contiguous all‐carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, render it a particularly challenging synthetic target among angular triquinane natural products. Here, we show that its polycyclic frame can be assembled concisely by using a strategically chosen quaternary center to guide the formation of the other three through judiciously selected C−C bond formation reactions. Those events, which included a unique Conia‐ene cyclization and a challenging Pauson–Khand reaction, afforded a 17‐step synthesis of the molecule in enantioenriched form.