(4aS*,10aR*)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-one

Abstract

Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.003 Å; R factor = 0.045; wR factor = 0.125; data-to-parameter ratio = 12.3.The title compound, C 20 H 28 O 2 , is a new totarolone which was isolated from Tetraclinis articulata wood. The molecule forms an extended sheet of three fused rings which exhibit different conformations. The non-aromatic oxo-substituted ring has a screw boat conformation, while the central ring has a halfchair conformation. Molecules are linked to each other by intermolecular O-HÁ Á ÁO hydrogen bonds involving carbonyl and hydroxyl groups.

Crystal structure of (4bS,8aR)-1-isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexahydrophenanthren-2-yl acetate

“…One with a similar conformation has a hydroxyl substituent in place of the acetate in the title compound (Benharref et al, 2011), and three others have a methoxy group in position 4b and carbaldehyde/benzenesulfonohydrazide (Vo et al, 2008) or biphenylsulfonyl (Gu & You, 2011) in position 9 ( Fig. 4b), while six entries (Oubabi et al, 2014a,b;Zeroual et al, 2007Zeroual et al, , 2008Cutfield et al, 1974;Pettit et al, 2004) have 1-isopropyl-4b,8,8-trimethyl substituents ( Fig. 4c).…”

7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-phenanthren-2(1H)-one

“…For their use in traditional medicine, see: Bellakhdar (1997) and for their medicinal properties, see: Barrero et al (2003); Comte et al (1995); Evidente et al (1997). For the synthesis see: Zeroual et al (2007). For conformational analysis, see: Cremer & Pople (1975).…”

“…In order to isolate similar compounds, we have studied the chloroform extract of Tetraclinis articulata wood. Thus, the extraction with chloroform using a soxhlet apparatus allow us isolate the totarolenone (7-hydroxy-8-isporpyl-1,1,4a-trimethyl-4a,9,10,10a-tetrahydro-1H-phenanthren-3-one) a derivative of totarolone (7-hydroxy-8-isporpyl-1,1,4a-trimethyl-3,4,4a,9,10,10a-hexahydophenantren-2-one) (Zeroual et al, 2007).…”