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Stereochemistry at C-11 and C-12 in the biosynthesis of olean-12-ene, urs-12-ene, and ?-sitosterol from [5-13C,5-2H2]mevalonolactone in tissue cultures of Isodon japonicus Hara

✍ Scribed by Seo, Shujiro; Tomita, Yutaka; Tori, Kazuo; Yoshimura, Yohko

Book ID: 126985282
Publisher: The Royal Society of Chemistry
Year: 1980
Tongue: English
Weight: 312 KB
Volume: 24
Category: Article
ISSN: 0022-4936
DOI: 10.1039/c39800001275

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Electrophilic and oxidative chemistry of

Electrophilic and oxidative chemistry of pyrene and its non-alternant isomers: theoretical (DFT, GIAO-NMR, NICS) study of protonation carbocations and oxidation dications from pyrene, azupyrene (dicyclopenta[ef,kl]heptalene) and dicyclohepta[ed,gh]pentaleneElectronic supplementary information (ESI) available: Table S1: Electronic energies (E), zero point energies (ZPE) and Gibbs free energies (G) obtained from DFT calculations for the studied molecules and cations at B3LYP/6-31G(d) level. Figs. S1, S8 and S10 and Tables S2?S14: Optimized structures and Cartesian coordinates for 1, 1aH+, 1bH22+, 12+, 2, 2aH+, 2aH22+, 22+, 3, 3cH+, 3eH22+ and 32+. Figs. S2, S3 and S4: Computed 13C NMR chemical shifts and NPA-derived charges for 1aH+, 122+ and 12+. Fig. S5: Experimental 13C NMR chemical shifts for 1aH+ and 12+. Figs. S6, S7, and S12: HOMO?LUMO forms in the oxidation dications. Figs. S9 and S11: Bond-lengths in X-ray derived and computed structures for 2 and 3. See http://www.rsc.org/suppdata/ob/b4/b405009f/

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