A new framework for the cycloaromatization of enediynes under mild conditions

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5583-5586

  Semmelhack, M F ^a   Gu, Yansong ^a   Ho, Douglas M ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CALICHEAMICIN; POLYCYCLIC AROMATIC COMPOUND; TOXIN;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030761988     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01263-X     Document Type: Article

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33. It is interesting to note that while 27 is relatively stable toward thermally-induced cycloaromatization, the product (33) from such a process was isolated in 74% yield when the ring closure was carried out with a large excess (16 mol-eq) of Cr(II) at 25 °C. Presumably, the cyclized product 27 forms and is then induced by the Cr(II) to cycloaromatize, by an unknown mechanism. (matrix presented)
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38. Acknowledgement: We wish to thank the National Institutes of Health for generous support of this work.