Journal of the American Chemical Society
Communication
spectral properties in excellent agreement with those derived
(12) (a) Mori, K. Tetrahedron: Asymmetry 2005, 16, 1721. (b) Yadav,
J. S.; Basak, A. K.; Srihari, P. Tetrahedron Lett. 2007, 48, 2841.
1
13
from the natural product [i.e., H and C NMR (500 and 125
MHz, respectively), HRMS parent ion identification, and
chiroptic properties].
In summary, the first total synthesis of a member of the
calyciphylline alkaloids, (−)-calyciphylline N (1), has been
achieved with a longest linear sequence of 37 steps from known
alcohol (−)-8. Application of the strategies presented herein for
the synthesis of other members of the Daphniphyllum alkaloids
continues in our laboratory.
(
(
(
(
(
(
(
13) Birch, A. J. J. Chem. Soc. 1944, 430.
14) Pearson, D. E.; Buehler, C. A. Chem. Rev. 1974, 74, 45.
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4387.
(
(
(
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22) A similar observation was noted in a recent total synthesis of
ASSOCIATED CONTENT
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*
S
Supporting Information
Maoecrystal V: Lu, P.; Gu, Z.; Zakarian, A. J. Am. Chem. Soc. 2013,
135, 14552.
(23) Tamao, K.; Yamauchi, T.; Ito, Y. Chem. Lett. 1987, 171.
Experimental details, spectra, and X-ray crystallographic data
(
24) Smith, A. B.; Hoye, A. T.; Martinez-Solorio, D.; Kim, W. S.;
Tong, R. B. A. J. Am. Chem. Soc. 2012, 134, 4533.
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AUTHOR INFORMATION
1974, 96, 7765.
(26) Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc. Chem. Commun.
1984, 29.
(
27) (a) Mitsunobu, O. Synthesis 1981, 1. (b) Mitsunobu, O.;
Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
28) Wu, Y. K.; Huang, J. H.; Shen, X.; Hu, Q.; Tang, C. J.; Li, L. Org.
Notes
The authors declare no competing financial interest.
(
Lett. 2002, 4, 2141.
ACKNOWLEDGMENTS
(29) Keinan, E.; Greenspoon, N. J. Am. Chem. Soc. 1986, 108, 7314.
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(30) Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc.
Financial support was provided by the National Institutes of
Health (National Cancer Institute) through CA-19033. We also
thank Drs. George Furst, Rakesh Kohli, and Patrick Carroll for
help in obtaining high-resolution NMR, mass spectral, and X-
ray crystallographic data, respectively.
1
968, 90, 5616.
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3912.
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(
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dx.doi.org/10.1021/ja411539w | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX