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Tarapacol 15-Acetate, a New Diterpenoid from Grindelia tarapacana Phil.
Zhou, Lin Timmermann, Barbara N. Grittini, Carina Bruck, Michael A. Enemark, John H.
Zhou, Lin
Timmermann, Barbara N.
Grittini, Carina
Bruck, Michael A.
Enemark, John H.
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Abstract
In the title compound, 15-acetoxy-14(S)-hydroxy-13-epi-manoyl oxide {IUPAC systematic name: 2-(dodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-3-yl)-2-hydroxyethyl acetate}, C22H38N4, rings A and B have chair conformations. Ring C adopts a boat conformation with the 16-methyl group in an axial position and the bulky glycol monoacetate group in an equatorial position. Ring systems A/B and B/C (conventional IUPAC labdane diterpenoid nomenclature) are trans fused about the C(5)-C(10) and C(8)-C(9) bonds, respectively. The present study establishes the relative stereochemistry at the C(14) position.
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1996
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International Union of Crystallography
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Zhou, L., Timmermann, B.N., Grittini, C., Bruck, M.A., and Enemark, J.H. "Tarapacol 15-Acetate, a New Diterpenoid from Grindelia tarapacana Phil." Acta Cryst. (1996). C52, 1042-1044 http://dx.doi.org/10.1107/S0108270195013473