Palladium-Catalyzed Routes to Geranylated or Farnesylated Phenolic Stilbenes: Synthesis of Pawhuskin C and Schweinfurthin J

Mandeep Singh; Narshinha P. Argade

doi:10.1055/s-0032-1316765

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(18): 2895-2902
DOI: 10.1055/s-0032-1316765

paper

Palladium-Catalyzed Routes to Geranylated or Farnesylated Phenolic Stilbenes: Synthesis of Pawhuskin C and Schweinfurthin J

Mandeep Singh

Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India, Fax: +91(20)25902629 eMail: np.argade@ncl.res.in

,

Narshinha P. Argade*

Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India, Fax: +91(20)25902629 eMail: np.argade@ncl.res.in

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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 - phloroglucinol

Volltext

Referenzen

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

40a Flaherty DP, Kiyota T, Dong Y, Ikezu T, Vennerstrom JL. J. Med. Chem. 2010; 53: 7992
40b Flaherty DP, Dong Y, Vennerstrom JL. Tetrahedron Lett. 2009; 50: 6228

Zusatzmaterial

Supporting Information