Synthesis of a novel dicyano abietane analogue: A potential antiinflammatory agent

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3314-3316

  Honda, Tadashi ^a   Yoshizawa, Hidenori ^a   Sundararajan, Chitra ^a   Gribble, Gordon W ^a  

^a 6128 Burke Laboratory ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANO GROUPS; NOVEL DICYANO ABIETANE ANALOGUE; PHENOLIC RING;

AROMATIZATION; MATHEMATICAL MODELS; OXIDATION; PEROXIDES; PHENOLS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

1,2,4A,9,10,10A HEXAHYDRO 6 HYDROXY 1,1,4A TRIMETHYL 2 OXOPHENANTHRENE 3,7 DICARBONITRILE; ABIETANE DERIVATIVE; ANTIINFLAMMATORY AGENT; CYANIDE; GAMMA INTERFERON; HYDROGEN PEROXIDE; NITRIC OXIDE; PHENYLSELENIUM CHLORIDE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; AROMATIZATION; ARTICLE; CELL LINE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTI-INFLAMMATORY AGENTS; DITERPENES, ABIETANE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION;

EID: 33645781250     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060059+     Document Type: Article

References (22)

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11. Synthesis of the methyl ester of 6 will be published elsewhere.
12. 3 in THF (rt, overnight), the methyl ester was recovered.
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17. 3. Because a hydroxyl group and an α-proton of cyano group of 8a were observed at δ 6.50 as a broad singlet and 4.21 as a double doublet (J = 14.3 and 4.76 Hz), respectively, although we concluded that 8a has one of two possible structures as shown below, we could not determine which structure corresponds to 8a. Because the two α-protons of the two cyano groups of 8b were observed at δ 4.26 (J = 15.0 and 4.39 Hz) and 4.06 (J = 13.9 and 5.13 Hz) as double doublets, respectively, we concluded that 8b has the structure as shown below with equatorial cyano groups. (Diagram presented)
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22. Overlapped signals which cannot be assigned.