C O M M U N I C A T I O N S
M. H. G.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258.
(f) Wigley, L. J.; Mantle, P. G.; Perry, D. A. Phytochemistry 2006, 67,
561.
In conclusion, we have accomplished the first total synthesis of
(-)-communesin F in 19 steps (longest linear sequence from
4-bromotryptophol) in ∼6% overall yield. Along with the total
synthesis, the absolute configuration of this natural product was
established, which will be helpful in solving the remaining
stereochemical questions for the other communesins as well as
perophoramidine. Our approach for efficiently constructing the G
and A rings will be of benefit for the assembly of the other members
of the communesin family, while our spiro-fused indoline formation
via an intramolecular oxidative coupling will stimulate further
applications in the syntheses of related indole alkaloids. Investiga-
tions in this direction are being actively pursued in our laboratory,
and the results will be disclosed in due course.
(2) For a brief review, see: Siengalewicz, P.; Gaich, T.; Mulzer, J. Angew.
Chem., Int. Ed. 2008, 47, 8170.
(3) (a) May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44,
1203. (b) Crawley, S. L.; Funk, R. L. Org. Lett. 2003, 5, 3169. (c) Yang,
J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006, 8, 2187. (d)
May, J. A.; Stoltz, B. M. Tetrahedron 2006, 62, 5262. (e) Seo, J. H.;
Artman, G. D., III; Weinreb, S. M. J. Org. Chem. 2006, 71, 8891. (f)
George, J. H.; Adlington, R. M. Synlett 2008, 2093. (g) Evans, M. A.;
Sacher, J. R.; Weinreb, S. M. Tetrahedron 2009, 65, 6712. (h) Seo, J. H.;
Liu, P.; Weinreb, S. M. J. Org. Chem. 2010, 75, 2667.
(4) Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794.
(5) Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000.
(6) (a) Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2004, 126, 7450. (b)
Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2005, 127, 15394. (c) Baran,
P. S. Angew. Chem., Int. Ed. 2005, 44, 609. (d) Baran, P. S.; DeMartino,
M. P. Angew. Chem., Int. Ed. 2006, 45, 7083. (e) Richter, J. M.; Whitefield,
B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am.
Chem. Soc. 2007, 129, 12875. (f) Richter, J. M.; Idhihara, Y.; Masuda, T.;
Whitefield, B. W.; Llamas, T.; Pohjakallio, A.; Baran, P. S. J. Am. Chem.
Soc. 2008, 130, 17938.
Acknowledgment. The authors are grateful to the National
BasicResearchProgramofChina(973Program,Grant2010CB833200),
the Chinese Academy of Sciences, and the National Natural Science
Foundation of China (Grants 20632050 and 20921091) for their
financial support.
(7) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Old, D. W.; Mooney, P. A.
J. Org. Chem. 1996, 61, 5813.
(8) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem.
Soc. 1998, 120, 6477.
(9) Fresneda, P. M.; Molina, P.; Delgado, S. Tetrahedron 2001, 57, 6197.
(10) (a) Eguchi, S.; Suzuki, T.; Okawa, T.; Matsushita, Y. J. Org. Chem. 1996,
61, 7316. (b) Foxman, H. F.; Snider, B. B. J. Am. Chem. Soc. 1998, 120,
6417. (c) Neubert, B. J.; Snider, B. B. Org. Lett. 2003, 5, 765. (d) Snider,
B. B.; Zeng, H. J. Org. Chem. 2003, 68, 545. For a review, see: (e) Palacios,
F.; Aparicio, D.; Rubiales, G.; Alonso, C.; Santos, J. M. Curr. Org. Chem.
2009, 13, 810.
(11) (a) Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068. For a
related study, see: (b) Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem.,
Int. Ed. 2006, 45, 4317.
(12) (a) Lei, Y.; Wrobleki, A. D.; Golden, J. E.; Powell, D. R.; Aube´, J. J. Am.
Chem. Soc. 2005, 127, 4552. (b) Kirby, A. J.; Komarov, I. V.; Feeder, N.
J. Chem. Soc. Perkin Trans. 2 2001, 522. (c) Wang, Q. P.; Bennett, A. J.;
Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757.
Supporting Information Available: Experimental and spectral data
for all new compounds and crystallographic data (CIF). This material
References
(1) (a) Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.;
Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993,
34, 2355. (b) Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schauman,
K.; Wray, V.; Steube, K.; Proksch, P. J. Nat. Prod. 2004, 67, 78. (c)
Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci., Biotechnol., Biochem.
2004, 68, 753. (d) Andersen, B.; Smedsgaard, J.; Frisvad, J. C. J. Agric.
Food Chem. 2004, 52, 2421. (e) Dalsgaard, P. W.; Blunt, J. W.; Munro,
JA106739G
9
13228 J. AM. CHEM. SOC. VOL. 132, NO. 38, 2010