Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method

Nicolas Zigon; Manabu Hoshino; Shota Yoshioka; Yasuhide Inokuma; Makoto Fujita

doi:10.1002/anie.201502302

Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method

Angew Chem Int Ed Engl. 2015 Jul 27;54(31):9033-7. doi: 10.1002/anie.201502302. Epub 2015 Jun 12.

Authors

Nicolas Zigon¹, Manabu Hoshino¹, Shota Yoshioka¹, Yasuhide Inokuma¹, Makoto Fujita²

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan).
² Department of Applied Chemistry, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). mfujita@appchem.t.u-tokyo.ac.jp.

PMID: 26072708
DOI: 10.1002/anie.201502302

Abstract

Crystal structures of α-humulene, a cyclic sesquiterpene, and its oxidized subproducts, were analyzed by the crystalline sponge method. Regio- and stereochemistry, including absolute configuration when a chiral oxidant was applied, and the stable conformations of all the scaffold-related compounds were successfully determined for samples on a 5-50 μg scale.

Keywords: configuration determination; crystalline sponge; host-guest systems; sesquiterpenes; structure elucidation.