Open AccessTarapacol 15‐Acetate, a New Diterpenoid from Grindelia tarapacana Phil .
Author(s) -
Zhou L.,
Timmermann B. N.,
Grittini C.,
Bruck M. A.,
Enemark J. H.
Publication year - 1996
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270195013473
Subject(s) - labdane , terpenoid , stereochemistry , ring (chemistry) , chemistry , diterpene , cyclohexane conformation , organic chemistry , molecule , hydrogen bond
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}, C22H38O4, 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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