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- Title
Lewis Acid Catalyzed, Selective Cyclopropane-Ring Opening in Ingol Diterpene Derivatives.
- Authors
Masuna Srinivasulu; Vanimireddy 4;Lakshmi 4;Niranjan Reddy; Samala 4;Malla Reddy; Veluri Ravikanth; Tuniki 4;Venugopal Raju; Sistla Ramakrishna; Yenamandra Venkateswarlu
- Abstract
Lewis acid mediated skeletal rearrangement of the ingol diterpenoids 1 and 4via regio- and stereospecific cyclopropane-ring opening afforded the four new compounds 2, 3, 5, and 6, named nivulianol A–D (Scheme 4;1). Their structures were established by means of IR, MS, and in-depth NMR spectroscopic analyses. The rearranged congeners were tested for lipopolysaccharide (LPS)-induced prostaglandin (PG) E2 (cyclooxygenase-2) inhibition. Thereby, nivulianol B (=(1S*,2E,4R*,5S*,7Z,9S*,11R,13S*,14S*)-14-acetoxy-5-methoxy-3,9,13-trimethyl-6-(1-methylethenyl)-10-oxo-15-oxatricyclo[9.3.1.01,11]pentadeca-2,7-dien-4-yl (2Z)-2-methylbut-2-enoate; 3) was found to be significantly active, with an IC50 value of 36.3 4;μg/ml.
- Publication
Helvetica Chimica Acta, 2005, Vol 88, Issue 9, p2527
- ISSN
0018-019X
- Publication type
Article