Synthesis of the C1–C12 Fragment of Calyculin C

Olga V. Konstantinova; Ari M.P. Koskinen

doi:10.1055/s-0037-1610387

Synthesis, Table of Contents

CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 285-295
DOI: 10.1055/s-0037-1610387

paper

Copyright with the author

Synthesis of the C1–C12 Fragment of Calyculin C

Olga V. Konstantinova

^aAalto University School of Chemical Engineering, Department of Chemistry and Materials Science, Kemistintie 1, P.O. Box 16100, 02150 Espoo, Finland Email: ari.koskinen@aalto.fi

^bLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia

,

Ari M.P. Koskinen *

^aAalto University School of Chemical Engineering, Department of Chemistry and Materials Science, Kemistintie 1, P.O. Box 16100, 02150 Espoo, Finland Email: ari.koskinen@aalto.fi

› Author Affiliations

Abstract

All articles of this category

Dedicated to the memory of Professor István E. Markó.

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A–J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx) being calyculins A and C. Herein, we demonstrate a concise route to access the C1–C12 tetraene fragment of calyculin C using transition-metal-catalyzed coupling reactions (Suzuki–Miyaura, Stille, Negishi and Heck) for the key connections. The synthesis starts from propionaldehyde and proceeds in 10 steps with 7.5% overall yield. We also describe an efficient route for the preparation of (Z)-3-iodobut-2-enenitrile in four steps and 68% yield.

Key words

calyculins - natural products - transition-metal-catalyzed cross-coupling - Suzuki–Miyaura - Stille - Negishi and Heck coupling - syntheses of di- and polyenes

Full Text

References

References

1a Kato Y, Fusetani N, Matsunaga S, Hashimoto K. J. Am. Chem. Soc. 1986; 108: 2780
1b Kato Y, Fusetani N, Matsunaga S, Hashimoto K, Koseki K. J. Org. Chem. 1988; 53: 3930
1c Calyculins E–H: Matsunaga S, Fujiki H, Sakata D, Fusetani N. Tetrahedron 1991; 47: 2999

2 Dumdei EJ, Blunt JW, Munro MH. G, Pannell LK. J. Org. Chem. 1997; 62: 2636
3 Matsunaga S, Wakimoto T, Fusetani N. J. Org. Chem. 1997; 62: 2640
4 Matsunaga S, Wakimoto T, Fusetani N, Suganuma M. Tetrahedron Lett. 1997; 38: 3763
5 Steube KG, Meyer C, Proksch P, Supriyono A, Sumaryono W, Drexler HG. Anticancer Res. 1998; 18: 129
6 Fu X, Schmitz FJ, Kelly-Borges M, McCready TL, Holmes CF. B. J. Org. Chem. 1998; 63: 7957
7 Wakimoto T, Egami Y, Abe I. Nat. Prod. Rep. 2016; 33: 751
8 Fagerholm AE, Habrant D, Koskinen AM.P. Mar. Drugs 2010; 8: 122
9 Evans DA, Gage JR, Leighton JL. J. Am. Chem. Soc. 1992; 114: 9434
10 Tanimoto N, Gerritz SW, Sawabe A, Noda T, Filla SA, Masamune S. Angew. Chem., Int. Ed. Engl. 1994; 33: 673
11 Yokokawa F, Hamada Y, Shioiri T. Chem. Commun. 1996; 871
12 Smith AB. III, Friestad GK, Duan JJ.-W, Barbosa J, Hull KG, Iwashima M, Qiu Y, Spoors PG, Bertounesque E, Salvatore BA. J. Org. Chem. 1998; 63: 7596
13 Ogawa AK, Armstrong RW. J. Am. Chem. Soc. 1998; 121: 12435
14 Anderson OP, Barrett AG. M, Edmunds JJ, Hachiya S.-I, Hendrix JA, Horita K, Malecha JW, Parkinson CJ, VanSickle A. Can. J. Chem. 2001; 79: 1562

Fragment A:

15a Koskinen AM.P, Chen J. Tetrahedron Lett. 1991; 32: 6977
15b Passiniemi M, Koskinen AM. P. Synthesis 2010; 2816

Fragment B:

15c Koskinen AM.P, Pihko PM. Tetrahedron Lett. 1994; 35: 7417
15d Pihko PM, Koskinen AM. P. J. Org. Chem. 1998; 63: 92

Fragment C:

15e Habrant D, Koskinen AM. P. Org. Biomol. Chem. 2010; 8: 4364

16 Pihko PM, Koskinen AM. P. Synlett 1999; 1966
17 Barrett AG. M, Edmunds JJ, Hendrix JA, Horita K, Parkinson CJ. J. Chem. Soc., Chem. Commun. 1992; 1238

18a Yokokawa F, Hamada Y, Shioiri T. Tetrahedron Lett. 1993; 34: 6559
18b Matsubara J, Nakao K, Shioiri T. Tetrahedron Lett. 1992; 33: 4187

19 Scarlato GR, DeMattei JA, Chong LS, Ogawa AK, Lin MR, Armstrong RW. J. Org. Chem. 1996; 61: 6139
20 Negishi E. Bull. Chem. Soc. Jpn. 2007; 80: 233
21 Ronson TO, Taylor RJ. K, Fairlamb IJ. S. Tetrahedron 2015; 71: 989
22 Heravi MM, Hashemi E, Azimian F. Tetrahedron 2014; 70: 7
23 Heravi MM, Hashemi E. Tetrahedron 2012; 68: 9145
24 Kosugi M, Fugami K. J. Organomet. Chem. 2002; 653: 50
25 Negishi E. Angew. Chem. Int. Ed. 2011; 50: 6738
26 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
27 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
28 Corey EJ, Katzenellenbogen JA, Posner GH. J. Am. Chem. Soc. 1967; 89: 4245
29 Betzer J.-F, Delaloge F, Muller B, Pancrazi A, Prunet J. J. Org. Chem. 1997; 62: 7768
30 Jung ME, Light LA. Tetrahedron Lett. 1982; 23: 3851
31 Zhang HX, Guibe F, Balavoine G. J. Org. Chem. 1990; 55: 1857
32 Huang Z, Negishi E. Org. Lett. 2006; 8: 3675

33a Cornil J, Echeverria P.-G, Phansavath P, Ratovelomanana-Vidal V, Guérinot A, Cossy J. Org. Lett. 2015; 17: 948
33b Madden KS, David S, Knowles JP, Whiting A. Chem. Commun. 2015; 51: 11409
33c Jeffery T. Tetrahedron Lett. 1985; 26: 2667

34 Desai NB, McKelvie N, Ramirez F. J. Am. Chem. Soc. 1962; 84: 1745
35 Roush WR, Moriarty KJ, Brown BB. Tetrahedron Lett. 1990; 31: 6509
36 Kim K, Lauher JW, Parker KA. Org. Lett. 2012; 14: 138
37 Sofiyev V, Navarro G, Trauner D. Org. Lett. 2008; 10: 149
38 Jacobsen MF, Moses JE, Adlington RM, Baldwin JE. Tetrahedron 2006; 62: 1675
39 Zeng X, Qian M, Hu Q, Negishi E. Angew. Chem. Int. Ed. 2004; 43: 2259
40 Källström S, Erkkilä A, Pihko PM, Sjöholm R, Sillanpää R, Leino R. Synlett 2005; 751
41 Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 13: 3769
42 Hart DW, Blackburn TF, Schwartz J. J. Am. Chem. Soc. 1975; 97: 679
43 Dale JA, Dull DL, Mosher HS. J. Org. Chem. 1969; 34: 2543
44 Ward DE, Rhee CK. Tetrahedron Lett. 1991; 32: 7165

45a Crossman JS, Perkins MV. J. Org. Chem. 2006; 71: 117
45b Brown HC, Bhat KS. J. Am. Chem. Soc. 1986; 108: 5919
45c Kalaitzakis D, Smonou I. Eur. J. Org. Chem. 2012; 43

46 Moure AL, Gómez Arrayás R, Cárdenas DJ, Alonso I, Carretero JC. J. Am. Chem. Soc. 2012; 134: 7219
47 Mitsudo T, Fischetti W, Heck RF. J. Org. Chem. 1984; 49: 1640
48 Okada A, Watanabe K, Umeda K, Miyakado M. Agric. Biol. Chem. 1991; 55: 2765
49 Zurwerra D, Gertsch J, Altmann K.-H. Org. Lett. 2010; 12: 2302
50 Yang Q, Draghici C, Njardarson JT, Li F, Smith BR, Das P. Org. Biomol. Chem. 2014; 12: 330
51 Placzek AT, Gibbs RA. Org. Lett. 2011; 13: 3576
52 Paterson I, Anderson EA, Dalby SM, Lim JH, Maltas P, Loiseleur O, Genovino J, Moessner C. Org. Biomol. Chem. 2012; 10: 5861

Supplementary Material

Supporting Information