Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(18): 2895-2902
DOI: 10.1055/s-0032-1316765
DOI: 10.1055/s-0032-1316765
paper
Palladium-Catalyzed Routes to Geranylated or Farnesylated Phenolic Stilbenes: Synthesis of Pawhuskin C and Schweinfurthin J
Further Information
Publication History
Received: 07 June 2012
Accepted after revision: 08 July 2012
Publication Date:
08 August 2012 (online)
![](https://www.thieme-connect.de/media/synthesis/201218/lookinside/thumbnails/10.1055-s-0032-1316765-1.jpg)
Abstract
Starting from double MOM-protected phloroglucinol, the facile total syntheses of bioactive natural products pawhuskin C and schweinfurthin J were accomplished in good overall yields. The Heck, Stille, or Suzuki coupling reactions of two different electron-rich phenolic segments bearing geranylated or farnesylated units were involved in the decisive step. The Sonogashira coupling reaction followed by palladium-catalyzed chemo- and stereoselective cis-reduction of an alkyne unit and subsequent isomerization to give the desired natural products is also described.
Key words
total synthesis - natural products - geranylated or farnesylated stilbenes - palladium-catalyzed coupling reactions - phloroglucinolSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Nicolaou KC, Evans RM, Roecker AJ, Hughes R, Downes M, Pfefferkorn JA. Org. Biomol. Chem. 2003; 1: 908 ; and references cited therein
- 2 Mondal M, Argade NP. Synlett 2004; 1243
- 3 Mondal M, Puranik VG, Argade NP. J. Org. Chem. 2006; 71: 4992
- 4 Mondal M, Puranik VG, Argade NP. J. Org. Chem. 2007; 72: 2068
- 5 Nicolaou KC, Lister T, Denton RM, Gelin CF. Angew. Chem. Int. Ed. 2007; 46: 7501
- 6 Qi J, Porco JA. Jr. J. Am. Chem. Soc. 2007; 129: 12682
- 7 Belofsky G, French AN, Wallace DR, Dodson SL. J. Nat. Prod. 2004; 67: 26
- 8 Klausmeyer P, Van Q N, Jato J, McCloud TG, Beutler JA. J. Nat. Prod. 2010; 73: 479
- 9a Neighbors JD, Buller MJ, Boss KD, Wiemer DF. J. Nat. Prod. 2008; 71: 1949
- 9b van der Kaaden JE, Hemscheidt TK, Mooberry SL. J. Nat. Prod. 2001; 64: 103
- 9c Treadwell EM, Cermak SC, Wiemer DF. J. Org. Chem. 1999; 64: 8718
- 10a Topczewski JJ, Kodet JG, Wiemer DF. J. Org. Chem. 2011; 76: 909
- 10b Yoder BJ, Cao S, Norris A, Miller JS, Ratovoson F, Razafitsalama J, Andriantsiferana R, Rasamison VE, Kingston DG. I. J. Nat. Prod. 2007; 70: 342
- 11 Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW. W, Fong HH. S, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM. Science (Washington, D.C.) 1997; 275: 218
- 12 Neighbors JD, Salnikova MS, Wiemer DF. Tetrahedron Lett. 2005; 46: 1321
- 13 Morales-Serna JA, Zúñiga-Martínez A, Salmón M, Gaviño R, Cárdenas J. Synthesis 2012; 44: 446 ; and references cited therein
- 14 Moro AV, Cardoso FS. P, Correia CR. D. Tetrahedron Lett. 2008; 49: 5668
- 15 Bazin M.-A, Kihel LE, Lancelot J.-C, Rault S. Tetrahedron Lett. 2007; 48: 4347
- 16 Takaoka S, Nakade K, Fukuyama Y. Tetrahedron Lett. 2002; 43: 6919
- 17 Castro AM. M. Chem. Rev. 2004; 104: 2939 ; and references cited therein
- 18 Vogel S, Heilmann J. J. Nat. Prod. 2008; 71: 1237
- 19a Cordes J, Calo F, Anderson K, Pfaffeneder T, Laclef S, White AJ. P, Barrett AG. M. J. Org. Chem. 2012; 77: 652
- 19b Sugamoto K, Matsusita Y.-I, Matsui K, Kurogi C, Matsui T. Tetrahedron 2011; 67: 5346
-
20 Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320
-
21 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009 ; and references cited therein
-
22 Milstein D, Stille JK. J. Am. Chem. Soc. 1978; 100: 3636
- 23 Farina V, Krishnamurthy V, Scott WJ. Org. React. 1998; 50: 1 ; and references cited therein
- 24 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
-
25 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457 ; and references cited therein
- 26 Wittig G, Schöllkopf U. Chem. Ber. 1954; 87: 1318
- 27 Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 28 Pietruszka J, Witt A. Synthesis 2006; 4266 ; and references cited therein
- 29 Powell DA, Maki T, Fu GC. J. Am. Chem. Soc. 2005; 127: 510
- 30 Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
- 31 Schlapbach A, Feifel R, Hawtin S, Heng R, Koch G, Moebitz H, Revesz L, Scheufler C, Velcicky J, Waelchli R, Huppertz C. Bioorg. Med. Chem. Lett. 2008; 18: 6142
- 32 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467
-
33 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874 ; and references cited therein
- 34 Deore PS, Argade NP. J. Org. Chem. 2012; 77: 739 ; and references cited therein
- 35 Boger DL, Boyce CW, Labroli MA, Sehon CA, Jin Q. J. Am. Chem. Soc. 1999; 121: 54
- 36 Al-Hassan MI. Synth. Commun. 1986; 16: 353
- 37 Li J, Hua R, Liu T. J. Org. Chem. 2010; 75: 2966
- 38a Yu J, Gaunt MJ, Spencer JB. J. Org. Chem. 2002; 67: 4627
- 38b Sen A, Lai T.-W. Inorg. Chem. 1981; 20: 4036
- 38c Sen A, Lai T.-W. Inorg. Chem. 1984; 23: 3257
- 39a Heynekamp JJ, Weber WM, Hunsaker LA, Gonzales AM, Orlando RA, Deck LM, Jagt DL. V. J. Med. Chem. 2006; 49: 7182
- 39b Chang S, Na Y, Shin HJ, Choi E, Jeong LS. Tetrahedron Lett. 2002; 43: 7445