Total synthesis and absolute configuration of laurenditerpenol: A hypoxia inducible factor-1 activation inhibitor

Journal of Medicinal Chemistry

Volumn 50, Issue 25, 2007, Pages 6299-6302

  Chittiboyina, Amar G ^a   Kumar, Gundluru Mahesh ^a   Carvalho, Paulo B ^a   Liu, Yang ^a   Zhou, Yu Dong ^a   Nagle, Dale G ^a   Avery, Mitchell A ^a,b,c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Environmental Toxicology Research Program   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYPOXIA INDUCIBLE FACTOR 1; LAURENDITERPENOL; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOLOGICAL ACTIVITY; BREAST TUMOR; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; TUMOR CELL LINE;

CELL HYPOXIA; CELL LINE, TUMOR; DITERPENES; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 37049013563     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm7011062     Document Type: Article

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40. Spectroscopic analysis and mechanistic implications of these kind of systems are under progress, and the detailed results will be explored elsewhere in the future.
41. To improve the epimerized product yield, several basic conditions were attempted. Either similar yield or decomposed product(s) especially with metal hydrides in aprotic solvents was obtained. It was determined at this stage to use this quick and processible reaction, albeit to provide the material for exploration.
42. See Supporting Information for a complete set of spectral data. Regarding the rotation value, variation in rotation value from reported 1 and synthesized 1c may be due to nonidentical experimental conditions. When we recorded the rotation of our authentic sample and synthetic sample under identical experimental conditions, the rotation value is identical.
43. For experimental details, see Supporting Information.
44. 50 value (0.4 μM) from a series of independent experiments was ultimately reported. This variation in potency is within the range of values observed in the original studies.