Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Synthesis of Benzo[c]Phenanthridine Alkaloids, Using a Novel Palladium-Phosphine Combination System - Pd(OAc)2, DPPP, and Bu3P Takashi Harayama*, Toshihiko Akiyama, Yuichiro Nakano, Kentaro Shibaike, Hisashi Akamatsu, Akihiro Hori, Hitoshi Abe, Yasuo TakeuchiFaculty of Pharmaceutical Sciences, Okayama University, Tsushima-naka 1-1-1, Okayama 700-8530, JapanFax: +81(86)2517963; e-Mail: harayama@pharm.okayama-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract Total synthesis of several benzo[c]phenanthridine alkaloids was accomplished via an aryl-aryl coupling reaction using a novel Pd reagent prepared from Pd(OAc)2, DPPP, and Bu3P. This is a versatile method for the coupling reactions of not only aryl triflates and arenes but also aryl halides and arenes. Key words intramolecular aryl-aryl coupling - ring closure - palladium reagent - halo-amide - triflate-amide Full Text References References 1a Simanek V. The Alkaloids Vol. 26: Brossi A. Academic Press; New York: 1985. p.185 1b Dostal J. Potacek M. Collect. Czech. Chem. Commun. 1990, 55: 2840 1c Suffiness M. Cordell G. The Alkaloids Vol. 25: Brossi A. Academic Press; New York: 1985. p.178 1d MacKay SP. Meth-Cohn O. Waigh RD. Adv. Heterocycl. Chem. 1997, 67: 345 1e Ishikawa T. Ishii H. Heterocycles 1999, 50: 627 1f Herert JM. Augereau J. Gleye JP. Maffrand J. Biochem. Biophys. Res. Commun. 1990, 172: 993 1g Fang S.-D. Wang L.-K. Hecht SM. J. Org. Chem. 1993, 58: 5025 1h Nakanishi T. Suzuki M. J. Nat. Prod. 1998, 61: 1263 1i Vavreckova C. Gawlik I. Müller K. Planta Med. 1996, 62: 397 1j Schmeller T. Latz-Bruning B. Wink M. Phytochemistry 1997, 44: 257 1k Nakanishi T. Suzuki M. Saimoto A. Kabasawa T. J. Nat. Prod. 1999, 62: 864 ; and references cited therein 1l Fleury F. Sukhanova A. Ianoul A. Devy J. Kudelina I. Duval O. Alix A. Jardillier J. Nabiev I. J. Biol. Chem. 2000, 275: 3501 Recent papers for synthesis of benzo[c]phenanthridine alkaloids: 2a Moreno I. Tellitu I. Etayo J. SanMartin R. Domingueez E. Tetrahedron 2001, 57: 5403 ; and references cited therein 2b Nakanishi T. Suzuki M. Org. Lett. 1999, 1: 985 ; and references cited therein 2c Geen GR. Mann IS. Mullane VM. McKillop A. Tetrahedron 1998, 54: 9875 2d Ishikawa T. Saito T. Ishii H. Tetrahedron 1995, 51: 8447 2e Minami T. Nishimoto A. Hanaoka M. Tetrahedron Lett. 1995, 36: 9505 ; and references cited therein 2f Seraphin D. Lynch MA. Duval O. Tetrahedron Lett. 1995, 36: 5731 2g Lynch MA. Duval O. Pochet P. Waigh RD. Bull. Soc. Chim. Fr. 1994, 131: 718 3a Harayama T. Akiyama T. Akamatsu H. Kawano K. Abe H. Takeuchi Y. Synthesis 2001, 444 3b Harayama T. Shibaike K. Heterocycles 1998, 49: 191 3c Harayama T. Akamatsu H. Okamura K. Miyagoe T. Akiyama T. Abe H. Takeuchi Y. J. Chem. Soc., Perkin Trans. 1 2001, 523 4 Harayama T. Akiyama T. Nakano Y. Chem. Pharm. Bull. 1997, 45: 1723 5 Ishii H. Kenmotsu K. Döpke W. Harayama T. Chem. Pharm. Bull. 1992, 40: 1770 6 Sihababu AK. Borchardt RT. J. Org. Chem. 1983, 48: 1941
