6,6,9a-Trimethyl-5,5a,6,7,8,9,9a,9b-octahydronaphtho[1,2-c]furan-1(3H)-one

Abstract

In the crystal structure of the title compound, C15H22O2, the cyclo­hexene and cyclo­hexane rings adopt half-boat and chair conformations, respectively, and the lactone ring is in an envelope conformation.

Drimane Sesquiterpenoids Noncompetitively Inhibit Human α4β2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human α3β4 and α7 Subtypes

“…The chemical characterization of drimane sesquiterpenoids coincides with that obtained by X-ray studies, − where a basic structural framework is shown: a trans -decalin moiety with a Δ 7(8) double bond, giving a twisted chair conformation at the second ring and conferring a planar C-7–C-8–C-12 dihedral angle of 126.7° for dendocarbin A.…”

“…The drimane sesquiterpenoids drimenin, cinnamolide, dendocarbin A, and polygodial (Figure 1) were isolated from EtOAc extracts of the bark from the Canelo tree D. winteri. The 1 H NMR (Table S1, Supporting Information) and 13 C NMR (Table S2, Supporting Information) results are in excellent agreement with previous data. 11 ,12 The chemical characterization of drimane sesquiterpenoids coincides with that obtained by X-ray studies, 13−15 where a basic structural framework is shown: a trans-decalin moiety with a Δ 7 (8) double bond, giving a twisted chair conformation at the second ring and conferring a planar C-7−C-8−C-12 dihedral angle of 126.7°for dendocarbin A.…”

“…The 1 H and 13 C NMR spectra were recorded in CD 2 Cl 2 or CDCl 3 solution in 5 mm tubes at room temperature on a Bruker Avance III spectrometer (Bruker Biospin GmbH, Rheinstetten, Germany) at 600.13 ( 1 H) and 150.61 ( 13 C) MHz, with the deuterium signal of the solvent as the lock and tetramethylsilane (for 1 H) or the solvent (for 13 C) as internal standard. All spectra ( 1 H, 13 C, gs-H,H− COSY, edited HSQC, and gs-HMBC) were acquired and processed with the standard Bruker software. The 1 H and 13 C NMR results are summarized in Tables S1 and S2 (Supporting Information), respectively.…”

“…All spectra ( 1 H, 13 C, gs-H,H− COSY, edited HSQC, and gs-HMBC) were acquired and processed with the standard Bruker software. The 1 H and 13 C NMR results are summarized in Tables S1 and S2 (Supporting Information), respectively.…”

Dendocarbin A: a sesquiterpene lactone fromDrimys winteri

“…It is worth mentioning that this envelope geometry for the lactone ring is favoured by the 'outer' position of the double bond; when the location is instead 'inner' (C8 C9), the group is strictly planar, with mean deviations from planarity smaller than 0.02 Å (see, for example, Nicotra et al, 2006;Qian & Zhao, 2012;von Nussbaum et al, 2012) A search of the Cambridge Structural Database (CSD, Version 5.34; Allen, 2002) disclosed that the structure of (I) is closely related to three analogues, viz. the disteromer lactone drimenin [(II); CSD refcode DIWSEI; Brito, Ló pez- Rodríguez et al, 2008] The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).…”