A Simple Synthesis of (±)-Sarkomycin

Anirban Kar; Narshinha P. Argade

doi:10.1055/s-2005-861877

SHORTPAPER

A Simple Synthesis of (±)-Sarkomycin [1]

Anirban Kar, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25893153; e-Mail: argade@dalton.ncl.res.in ;

Abstract

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Abstract

A facile 6-step route to (±)-sarkomycin in 17% overall yield has been described via Michael addition of nitromethane to 2-hydroxymethyl-2-cyclopentenone, oxone-induced oxidative Nef reaction, and acid catalyzed dehydration.

Key words

2-hydroxymethyl-2-cyclopentenone - nitromethane - Michael addition - oxidative Nef reaction - oxone - (±)-sarkomycin synthesis

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References

NCL Communication No. 6675.

<A NAME="RZ16704SS-2A">2a</A> Yamamoto T. Yamaoka S. J. Antibiot. Ser. A. 1954, 7: 7

<A NAME="RZ16704SS-2B">2b</A> Umezawa H. Takeuchi T. Nitta K. J. Antibiot. Ser. A. 1953, 6: 101

<A NAME="RZ16704SS-2C">2c</A> Umezawa H. Yamamoto T. Takeuchi T. Yamaoka S. Nitta K. Okami Y. J. Antibiot. Ser. A. 1953, 6: 147

<A NAME="RZ16704SS-3">3</A> Umezawa H. Yamamoto T. Takeuchi T. Osato T. Okami Y. Yamaoka S. Okuda T. Nitta K. Yagishita K. Utahara R. Umezawa S. Antibiot. Chemother. 1954, 4: 514

<A NAME="RZ16704SS-4">4</A> Sung SC. Quastel JH. Cancer Res. 1963, 23: 1549

<A NAME="RZ16704SS-5">5</A> Hooper IR. Chenyl LC. Cron MJ. Fardig OB. Johnson DA. Johson DL. Patermiti FM. Schmitz H. Wheatley WB. Antibiot. Chemother. 1955, 5: 585

<A NAME="RZ16704SS-6">6</A> Hill RH. Foley PJ. Gardella LA. J. Org. Chem. 1967, 32: 2330

<A NAME="RZ16704SS-7A">7a</A> Boeckman RK. Naegely PC. Arthur SD. J. Org. Chem. 1980, 45: 752

<A NAME="RZ16704SS-7B">7b</A> Marx JN. Minaskanian G. J. Org. Chem. 1982, 47: 3306

<A NAME="RZ16704SS-7C">7c</A> Wexler BA. Toder BH. Minaskanian G. Smith AB. J. Org. Chem. 1982, 47: 3333

<A NAME="RZ16704SS-7D">7d</A> Kobayashi Y. Tsuji J. Tetrahedron Lett. 1981, 22: 4295

<A NAME="RZ16704SS-7E">7e</A> Barreiro EJ. Tetrahedron Lett. 1982, 23: 3605

<A NAME="RZ16704SS-7F">7f</A> Govindan SV. Hudlicky T. Koszyk FJ. J. Org. Chem. 1983, 48: 3581

<A NAME="RZ16704SS-7G">7g</A> Hewson AT. MacPherson DT. Tetrahedron Lett. 1983, 24: 647

<A NAME="RZ16704SS-7H">7h</A> Misumi A. Furuta K. Yamamoto H. Tetrahedron Lett. 1984, 25: 671

<A NAME="RZ16704SS-7I">7i</A> Kodpinid M. Siwapinyoyos T. Thebtaranonth Y. J. Am. Chem. Soc. 1984, 106: 4862

<A NAME="RZ16704SS-7J">7j</A> Mikolajczyk M. Zurawinski R. Kielbasinski P. Tetrahedron Lett. 1989, 30: 1143 ; and references cited therein 7a-j

<A NAME="RZ16704SS-8A">8a</A> Kozikowski AP. Stein PD. J. Am. Chem. Soc. 1982, 104: 4023

<A NAME="RZ16704SS-8B">8b</A> Froissant J. Huet F. Conia JM. Nouv. J. Chim. 1983, 7: 699

<A NAME="RZ16704SS-8C">8c</A> Vidal J. Huet F. Tetrahedron Lett. 1986, 27: 3733

<A NAME="RZ16704SS-8D">8d</A> Froissant J. Vidal J. Guibe-Jampel E. Huet F. Tetrahedron 1987, 43: 317

<A NAME="RZ16704SS-8E">8e</A> Amri H. Rambaud M. Villieras J. Tetrahedron Lett. 1989, 30: 7381

<A NAME="RZ16704SS-9A">9a</A> Samarat A. Fargeas V. Villieras J. Lebreton J. Amri H. Tetrahedron Lett. 2001, 42: 1273

<A NAME="RZ16704SS-9B">9b</A> Samarat A. Landais Y. Amri H. Tetrahedron Lett. 2004, 45: 2049

<A NAME="RZ16704SS-10A">10a</A> Gogoi S. Argade NP. Tetrahedron 2004, 60: 9093

<A NAME="RZ16704SS-10B">10b</A> Mondal M. Argade NP. Tetrahedron Lett. 2004, 45: 5693

<A NAME="RZ16704SS-10C">10c</A> Mhaske SB. Argade NP. J. Org. Chem. 2004, 69: 4563

<A NAME="RZ16704SS-10D">10d</A> Mondal M. Argade NP. Synlett 2004, 1243

<A NAME="RZ16704SS-10E">10e</A> Mangaleswaran S. Argade NP. Synthesis 2004, 1560

<A NAME="RZ16704SS-10F">10f</A> Mhaske SB. Argade NP. Tetrahedron 2004, 60: 3417

<A NAME="RZ16704SS-10G">10g</A> Kar A. Argade NP. Tetrahedron 2003, 59: 2991 ; and references cited therein 10a-g

<A NAME="RZ16704SS-11">11</A> Gatri R. ElGaïed MM. Tetrahedron Lett. 2002, 43: 7855

<A NAME="RZ16704SS-12A">12a</A> Rezgui F. ElGaïed MM. Tetrahedron Lett. 1998, 39: 5965

<A NAME="RZ16704SS-12B">12b</A> Kataoka T. Iwama T. Tsujiyama S. Iwamura T. Watanabe S. Tetrahedron 1998, 54: 11813

<A NAME="RZ16704SS-12C">12c</A> Iwama T. Kinoshita H. Kataoka T. Tetrahedron Lett. 1999, 40: 3741

<A NAME="RZ16704SS-12D">12d</A> Li G. Wei H. Gao JJ. Caputo TD. Tetrahedron Lett. 2000, 41: 1

<A NAME="RZ16704SS-13">13</A> Crombie L. Heavers AD. J. Chem. Soc., Perkin. Trans. 1 1992, 2683

<A NAME="RZ16704SS-14">14</A> Ceccherelli P. Curini M. Marcotullio MC. Epifano F. Rosati O. Synth. Commun. 1998, 28: 3057