Synthesis of 13C2-benzo[a]pyrene and its 7,8-dihydrodiol and 7,8-dione implicated as carcinogenic metabolites

Tetrahedron Letters

Volumn 49, Issue 29-30, 2008, Pages 4531-4533

  Ran, Chongzhao ^a   Xu, Daiwang ^a   Dai, Qing ^a   Penning, Trevor M ^b   Blair, Ian A ^b   Harvey, Ronald G ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BENZO[A]PYRENE DERIVATIVE; BORONIC ACID DERIVATIVE; CARCINOGEN; KETONE DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CARCINOGENICITY; CATALYSIS; PHYSICAL CHEMISTRY; SUZUKI REACTION; WITTIG REACTION;

EID: 44749092323     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.033     Document Type: Article

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26. 3 and treatment of the resulting phosphonium salt with t-BuOK (Ref. 21a).
27. 3I (2.0 g, 4.9 mmol) in anhydrous THF (20 mL) at -78 °C under argon was added a solution of n-BuLi (2.0 mL of a 2.5 M solution in THF, 5.0 mmol). The solution was stirred at -78 °C for 20 min, then the cooling bath was removed, and stirring was continued for an additional 30 min.
28. 3) δ 114.7. This compound was unstable and deteriorated on standing.
29. 3) δ 122.1 and 128.1.
30. A suspension of 6b (40 mg, 0.14 mmol) in 57% HI (5 mL) and HOAc (5 mL) was stirred at 140 °C until TLC showed reaction to be complete (1.5 h). Then the solution was cooled to room temperature, and poured into ice water (50 mL) to afford 6c (37 mg, 97%) which was used directly in the next step.
31. 13C-atoms in the C-5 and C-11-positions.
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33. 13C-atoms in the C-5 and C-11-positions.
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