Organic Letters
Letter
However, the biological activity reported in this manuscript was not
specifically called into question and is distinct relative to previous
reports.1
Scheme 7. Formal Synthesis of Perophoramidine (2)
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the formal syntheses of both communesin F and perophor-
amidine.
ASSOCIATED CONTENT
* Supporting Information
■
S
The authors declare no competing financial interest. This
material is available free of charge via the Internet at http://pubs.
AUTHOR INFORMATION
Corresponding Author
■
Notes
(8) (a) Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677. (b) Dou, X.;
Yao, W.; Zhou, B.; Lu, Y. Chem. Commun. 2013, 49, 9224.
(9) Marfat, A.; Carta, M. P. Tetrahedron Lett. 1987, 28, 4027.
(10) (a) Snider, B. B.; Busuyek, M. V. Tetrahedron 2001, 57, 3301.
(b) Gareau, Y.; Zamboni, R.; Wong, A. W. J. Org. Chem. 1993, 58, 1582.
(c) Voelker, T.; Ewell, T.; Joo, J.; Edstrom, E. D. Tetrahedron Lett. 1998,
39, 359.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors wish to thank NIH-NIGMS (R01GM080269),
Amgen, the Gordon and Betty Moore Foundation, and Caltech
for financial support. S.-J.H. thanks Fulbright (Foreign Student
Program, No. 15111120) and the Ilju Foundation of Education
& Culture (Predoctoral Research Fellowship) for financial
support. F.V. thanks the German Academic Exchange Service
(DAAD) (postdoctoral fellowship). S.K. thanks California
TRDRP for financial support (postdoctoral fellowship 14FT-
0002). J.A.M. is grateful for a fellowship by Bristol-Myers Squibb
and Amgen. M.G. is grateful to the Swiss National Science
Foundation for financial support (postdoctoral fellowship). Dr.
David VanderVelde (Caltech) is gratefully acknowledged for
assistance with the characterization of compounds by NMR
spectroscopy. Lawrence Henling (Caltech) is acknowledged for
X-ray crystallographic structural determination.
(11) Explorations in our laboratory regarding the generality of this
deprotection method are ongoing.
(12) Despite the high levels of diastereocontrol observed in the allylic
alkylations described in this manuscript (i.e., 11 → 4 and 22 → 21), a
reasonable explanation for these selectivities has not been as
forthcoming. Investigations into these fascinating reactions and the
underlying principles guiding the observed stereoselectivities are
ongoing.
(13) Fukuyama, T.; Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
(14) (a) Trost, B. M.; Malhotra, S.; Chan, W. H. J. Am. Chem. Soc.
2011, 133, 7328. (b) Li, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011,
50, 6396.
(15) Wang, Y.; Kong, C.; Du, Y.; Song, H.; Zhang, D.; Qin, Y. Org.
Biomol. Chem. 2012, 10, 2793.
(16) Yamada, Y.; Arima, S.; Okada, C.; Akiba, A.; Kai, T.; Harigaya, Y.
Chem. Pharm. Bull. 2006, 54, 788.
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