Journal of the American Chemical Society
Article
kinamycin and lomaiviticin D-ring precursors 60 and 68, and
implementation of a convergent, three-step strategy for
construction of the diazofluorene functional group. Use of
substrate control to effect the transformation of the ketone 63
to the trans-1,2-diol 67, in the presence of the redox-sensitive
diazofluorene, allowed for a short synthesis of (−)-kinamycin F
(9, 13 steps from m-cresol).
138425). S.B.H. is a fellow of the David and Lucile Packard and
the Alfred P. Sloan Foundations, and is a Camille Dreyfus
Teacher−Scholar.
REFERENCES
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diazofluorenes may be possible.
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ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures and detailed characterization data of
all new compounds. This material is available free of charge via
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
(7) (a) Nicolaou, K. C.; Denton, R. M.; Lenzen, A.; Edmonds, D. J.;
Li, A.; Milburn, R. R.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45,
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Chem., Int. Ed. 2008, 47, 1680. (c) Morris, W. J.; Shair, M. D. Org. Lett.
2008, 11, 9. (d) Zhang, W.; Baranczak, A.; Sulikowski, G. A. Org. Lett.
2008, 10, 1939. (e) Gholap, S. L.; Woo, C. M.; Ravikumar, P. C.;
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ACKNOWLEDGMENTS
■
Financial support from the National Institute of General
Medical Sciences (R01GM090000), the National Science
Foundation (Graduate Research Fellowship to C.M.W.), the
Searle Scholars Program, and Yale University is gratefully
acknowledged. We thank Dr. Gil Mor and Dr. Ayesha Alvero
for determining the activity of 103 against ovarian CSCs and
Dr. Eric Paulson of the Yale Chemical and Biophysical
Instrumentation Center for assistance with NMR. We acknowl-
edge the Developmental Therapeutics Program of the National
Cancer Institute for a gift of (−)-kinamycin C (8, NSC
17272
dx.doi.org/10.1021/ja307497h | J. Am. Chem. Soc. 2012, 134, 17262−17273