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1. Synthesis of anti-Helicobacter pylori sesquiterpene employing tandem radical cyclization, and determination of the absolute configuration of the natural product

Author

Shohei Aiba, Shinya Yamada, Hirosato Takikawa, Tsuneomi Kawasaki, Ken Ishigami, Arata Yajima, Ryo Katsuta, Kazuki Kadowaki, Tomoo Nukada, and Hidenori Watanabe

Subjects
Heptane, Natural product, Tandem, Bicyclic molecule, 010405 organic chemistry, Stereochemistry, Organic Chemistry, Absolute configuration, 010402 general chemistry, Sesquiterpene, 01 natural sciences, Biochemistry, Radical cyclization, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Drug Discovery, Enantiomer
Abstract

Both enantiomers of (Z)-2β-hydroxy-14-hydro-β-santalol, a potent anti-H. pylori agent, were synthesized and the absolute configuration of the natural product was determined to be 1R,2S,3R,4S. The bicyclo[2.2.1]heptane skeleton was efficiently constructed employing tandem radical cyclization of tethered precursor. Both enantiomers were prepared via optical resolution of racemic intermediate.

Published
2020
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