Efficient synthetic strategies for several bioactive alkaloids bearing a spirocyclic ring system have been developed. By application of an intramolecular aromatic oxidation of a phenolic intermediate, derived from l-tyrosine and glycine, with hypervalent iodine reagents, TAN1251A, isolated from Penicillium thomii RA-89, was synthesized in an optically pure form. Similarly, a novel synthetic path to TAN1251C and TAN1251D was established by employing an l-tyrosine dimer as a common starting material. Moreover, an enamide-phenol oxidative coupling reaction was applied to the synthesis of spirocyclic isoquinoline alkaloids, stepharine and annosqualine. Finally, stereoselective syntheses of securinine and viroallosecurinine in optically active forms were established by using a tandem ring-closing metathesis (RCM) of the enyne as a key reaction.
Conference
International Congress on Heterocyclic Chemistry (ICHC-22), International Congress on Heterocyclic Chemistry, ICHC, Heterocyclic Chemistry, 22nd, St John's, Newfoundland and Labrador, Canada, 2009-08-02–2009-08-07
References
1 For reviews, see.Search in Google Scholar
1a M. Ochiai. Rev. Heteroatom. Chem.2, 92 (1989).Search in Google Scholar
1b 10.1055/s-1990-26898, R. M. Moriarty. Synthesis 431 (1990).Search in Google Scholar
1c 10.1055/s-1990-21097, R. M. Moriarty, R. K. Vaid, G. E. Koser. Synlett 365 (1990).Search in Google Scholar
1d Y. Kita, H. Tohma, T. Yakura. Trends Org. Chem.3, 113 (1992).Search in Google Scholar
1e 10.1021/cr940424+, P. J. Stang, V. V. Zhdankin. Chem. Rev.96, 1123 (1996).Search in Google Scholar
1f A. Varvogolis. Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego (1997).Search in Google Scholar
1g 10.1080/00304949709355217, T. Kitamura, Y. Fujiwara. Org. Prep. Proced. Int.29, 409 (1997).Search in Google Scholar
1h V. V. Zhdankin. ARKIVOC 1 (2009).10.3998/ark.5550190.0010.101Search in Google Scholar
2 H. Shirafuji, S. Tsubotani, T. Ishimaru, S. Harada. PTC Inc. Appl., 1991, WO91 13,887 [Chem. Abstr. 116, 39780h (1992)].Search in Google Scholar
3a 10.1016/S0040-4039(02)00296-4, H. Mizutani, J. Takayama, T. Honda. Tetrahedron Lett.43, 2411 (2002).Search in Google Scholar
3b H. Mizutani, J. Takayama, T. Honda. Heterocycles62, 343 (2004).10.3987/COM-03-S(P)14Search in Google Scholar
4 H. Mizutani, J. Takayama, T. Honda. Synlett 328 (2005).Search in Google Scholar
5 10.1016/S1359-6446(97)01076-3, D. Widzowski, H. F. Helander, E. S. C. Wu. Drug Discov. Today2, 341 (1997).Search in Google Scholar
6 10.1021/ol991401q, B. B. Snider, H. Lin. Org. Lett.2, 643 (2000).Search in Google Scholar PubMed
7 10.1021/ol015626o, D. J. Wardrop, A. Basek. Org. Lett.3, 1053 (2001).Search in Google Scholar PubMed
8 J. M. A. Auty, I. Churcher, C. J. Hayes. Synlett 1443 (2004).10.1055/s-2004-829092Search in Google Scholar
9 10.1021/ja016030z, M. Ousmer, N. A. Braun, C. Bavoux, M. Perrin, M. A. Ciufolini. J. Am. Chem. Soc.123, 7534 (2001).Search in Google Scholar
10 10.1016/S0040-4020(02)01292-9, S. Nagumo, A. Matoba, Y. Ishii, S. Yamaguchi, N. Akutsu, H. Nishijima, A Nishida, N. Kawahara. Tetrahedron58, 9871 (2002).Search in Google Scholar
11 10.1021/ja0009525, Y. Moritani, D. H. Appella, V. Jurkauskas, S. L. Buchwald. J. Am. Chem. Soc.122, 6797 (2000).Search in Google Scholar
12 V. V. Berezhinskaya, E. A. Trutneva. Tr. Vses. Nauchno-Issled. Inst. Lek. Rast.14, 66 (1971).Search in Google Scholar
13a T. Kametani, H. Yagi. Chem. Commun. 366 (1967).10.1039/C19670000366Search in Google Scholar
13b T. Kametani, H. Yagi. J. Chem. Soc., Perkin Trans. 2182 (1967).10.1039/J39670002182Search in Google Scholar
14a 10.1016/S0040-4039(01)96655-9, Z. Horii, Y. Nakashita, C. Iwata. Tetrahedron Lett.12, 1167 (1971).Search in Google Scholar
14b T. Kametani, T. Sugahara, H. Sugi, S. Shibuya, K. Fukumoto. Chem. Commun. 724 (1971).10.1039/C29710000724Search in Google Scholar
14c 10.1016/S0040-4020(01)91764-8, T. Kametani, T. Sugahara, H. Sugi, S. Shibuya, K. Fukumoto. Tetrahedron27, 5993 (1971).Search in Google Scholar
14d 10.1039/p19720001435, T. Kametani, K. Fukumoto, S. Shibuya, H. Nemoto, T. Nakano, T. Sugahara, T. Takahashi, Y. Aizawa, M. Toriyama. J. Chem. Soc., Perkin Trans. 1 1435 (1972).Search in Google Scholar PubMed
14e Z. Horii, C. Iwata, Y. Nakashita. Chem. Pharm. Bull.26, 481 (1978).Search in Google Scholar
15 S. Ishiwata, K. Itakura, K. Misawa. Chem. Pharm. Bull.18, 1219 (1970).Search in Google Scholar
16 For reviews, see.Search in Google Scholar
16a M. Shamma. Alkaloids (London) 6, 170 (1975).Search in Google Scholar
16b E. K. Stephenson, M. P. Cava. Heterocycles39, 891 (1994) and refs. cited therein.10.3987/REV-94-SR(B)3Search in Google Scholar
17 10.1021/ol052841m, T. Honda, H. Shigehisa. Org. Lett.8, 657 (2006).Search in Google Scholar
18 10.1002/hlca.200490127, Y.-L. Yang, F.-R. Chang, Y.-C. Wu. Helv. Chim. Acta87, 1392 (2004).Search in Google Scholar
19 10.1016/j.tetlet.2006.08.028, H. Shigehisa, T. Honda. Tetrahedron Lett.47, 7301 (2006).Search in Google Scholar
20 Russian Pharmacopeia, 10th ed., Ministry of Health of the USSR, Moscow, pp. 612–614 (1968).Search in Google Scholar
21 10.1016/0006-8993(85)90014-9, I. A. Beutler, E. W. Karbon, A. N. Brubaker, R. Malik, D. R. Curtis, S. J. Enna. Brain Res.330, 135 (1985).Search in Google Scholar
22 10.1021/ol0361251, T. Honda, H. Namiki, K. Kaneda, H. Mizutani. Org. Lett.6, 87 (2004).Search in Google Scholar PubMed
23 10.1002/jps.2600800408, H. Tatematsu, M. Mori, T.-H. Yang, J.-J. Chang, T. T.-Y. Lee, K.-H. Lee. J. Pharm. Sci.80, 325 (1991).Search in Google Scholar PubMed
24 10.1016/j.tetlet.2004.05.031, T. Honda, H. Namiki, M. Watanabe, H. Mizutani. Tetrahedron Lett.45, 5211 (2004).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
