Total synthesis of antofine using the net [5+5]-cycloaddition of γ,δ-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6682-6685

  Camacho Davila, Alejandro ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-ALKYNYLPHENYL KETONES; ANTICANCER AGENT; ANTOFINE; CARBENE COMPLEXES;

AGENTS; CARBON; DERIVATIVES; ONCOLOGY; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

KETONES;

ANTINEOPLASTIC AGENT; ANTOFINE; CARBENE; PHENYL KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

HYDROCARBONS; INDOLES; KETONES; METHANE; MOLECULAR STRUCTURE; PHENANTHROLINES;

EID: 33747433298     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061053n     Document Type: Article

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32. The overall synthesis is six steps from known compound 6, seven steps from commercially available 6-bromoveratraldehyde (5), and eight steps from cheap 3,4-dimethoxybenzaldehyde.
33. For a general experimental, see the Supporting Information.
34. See Supporting Information.
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37. The spectral data are not in agreement with that reported for this compound in ref 9. A closer examination reveals that the spectral data reported for compound 16 in ref 9 are actually the spectral data for antofine.
38. The yield for this process is reported as quantitative (see ref 9). Our yield was 75%; however, we only attempted this reaction once.