Beilstein J. Org. Chem. 2013, 9, 983–990.
12.Noble, R. L.; Beer, C. T.; Cutts, J. H. Ann. N. Y. Acad. Sci. 1958, 76,
13.Noble, R. L. Lloydia 1964, 27, 280.
developed. The “stop-and-flow” strategy allows us to easily
functionalize seco-dienes step-by-step. Moreover, this ap-
proach also chemoselectively functionalizes terminal alkenes
instead of internal ones. Substituted 5-hydroxymethyl-γ-
lactones have been constructed in a protecting-group-free
manner. The synthetic application in the efficient synthesis of
velbanamine-type indole alkaloids as well as the enantioselec-
tive desymmetrization are currently pursued in our laboratory
and will be reported in due course.
14.Svoboda, G. H.; Neuss, N.; Gorman, M. J. Am. Pharm. Assoc., Sci. Ed.
15.Neuss, N. Bull. Soc. Chim. Fr. 1962, 1509.
16.van Beck, T. A.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron
17.Buechi, G.; Kulsa, P.; Rosati, R. L. J. Am. Chem. Soc. 1968, 90, 2448.
18.Buechi, G.; Kulsa, P.; Ogasawara, K.; Rosati, R. L. J. Am. Chem. Soc.
19.Kutney, J. P.; Bylsma, F. J. Am. Chem. Soc. 1970, 92, 6090.
Supporting Information
20.Narisada, M.; Watanabe, F.; Nagata, W. Tetrahedron Lett. 1971, 12,
Supporting Information File 1
Experimental descriptions, analytical and X-ray data.
21.Kutney, J. P.; Bylsma, F. Helv. Chim. Acta 1975, 58, 1672.
22.Takano, S.; Hirama, M.; Ogasawara, K. J. Org. Chem. 1980, 45, 3729.
23.Takano, S.; Yonaga, M.; Chiba, K.; Ogasawara, K. Tetrahedron Lett.
24.Takano, S.; Uchida, W.; Hatakeyama, S.; Ogasawara, K. Chem. Lett.
Acknowledgements
We thank the National Natural Science Foundation of China
(21290184 and 21172236 to R. Hong, 20802070 to X. Wang)
and the Chinese Academy of Sciences for their generous finan-
cial support. We thank Dr. Xiaodi Yang (Fudan University) for
X-ray analysis and Dr. Rob Hoen (GP Pharm, Spain) for helpful
discussions.
25.Dewick, P. M. Medicinal Natural Products: A Biogenetic Approach, 2nd
ed.; John Wiley & Sons: New York, NY, USA, 2001; p 355.
26.Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev.
See for a review of osmium in the Upjohn dihydroxylation and
Sharpless dihydroxylation.
See for a synthetic method with manganese.
References
28.Park, C. P.; Lee, J. H.; Yoo, K. S.; Jung, K. W. Org. Lett. 2010, 12,
1. Neuss, N.; Neuss, M. N. In The Alkaloids; Brossi, A.; Suffness, M.,
Eds.; Academic Press: San Diego, CA, USA, 1990; Vol. 37, p 229.
2. Mangeney, P.; Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y.;
Potier, P. J. Am. Chem. Soc. 1979, 101, 2243.
See for a synthetic method with palladium.
29.Wang, A.; Jiang, H.; Chen, H. J. Am. Chem. Soc. 2009, 131, 3846.
See for a synthetic method with palladium.
3. Kutney, J. P.; Choi, L. S. L.; Nakano, J.; Tsukamoto, H.; McHugh, M.;
4. Kuehne, M. E.; Zebovitz, T. C.; Bornmann, W. G.; Marko, I.
5. Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. J. Org. Chem. 1991,
30.Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962.
See for a synthetic method with palladium.
31.Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 3076.
See for a synthetic method with palladium.
6. Bornmann, W. G.; Kuehne, M. E. J. Org. Chem. 1992, 57, 1752.
32.Plietker, B.; Niggemann, M. Org. Lett. 2003, 5, 3353.
7. Magnus, P.; Mendoza, J. S.; Stamford, A.; Ladlow, M.; Willis, P.
8. Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.;
Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137.
See for a synthetic method with ruthenium.
33.Göksel, H.; Stark, C. B. W. Org. Lett. 2006, 8, 3433.
See for a synthetic method with ruthenium.
34.Fujita, M.; Costas, M.; Que, L., Jr. J. Am. Chem. Soc. 2003, 125, 9912.
9. Kuboyama, T.; Yokoshima, S.; Tokuyama, H.; Fukuyama, T.
Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11966.
See for a synthetic method with iron.
35.Oldenburg, P. D.; Shteinman, A. A.; Que, L., Jr. J. Am. Chem. Soc.
10.Ishikawa, H.; Colby, D. A.; Boger, D. L. J. Am. Chem. Soc. 2008, 130,
See for a synthetic method with iron.
11.Ishikawa, H.; Colby, D. A.; Seto, S.; Va, P.; Tam, A.; Kakei, H.;
Rayl, T. J.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2009, 131, 4904.
36.Prévost, C. C. R. Hebd. Seances Acad. Sci. 1933, 196, 1129.
See for silver in the Prévost–Woodward reaction.
And references cited therein.
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