Synthesis of Chlorooxazoles Related to Natural Products

Alexander Radspieler; Jürgen Liebscher

doi:10.1055/s-2001-12771

PAPER

Synthesis of Chlorooxazoles Related to Natural Products

Alexander Radspieler, Jürgen Liebscher*
Institut für Chemie, Humboldt-Universität Berlin, Hessische Straße 1-2, 10115 Berlin, Germany
Fax: +49(30)20938907; e-Mail: liebscher@chemie.hu-berlin.de;

Abstract

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Abstract

2-Chloro-3-(4-chlorooxazole-5-yl)-indoles and 4-chloro-5-phenyl-oxazoles 3 were synthesised from acyl cyanides 1, aldehydes 2 and hydrogen chloride. By further derivatisation of the substituent at position 2 of the 4-chlorooxazole ring, useful potential building blocks 3l, 3n and 3o for a total synthesis of diazonamide A, were obtained.

Key words

4-chlorooxazoles - diazonamide A - acyl cyanides - indoles - heterocycles - synthesis

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References

<A NAME="RT04300SS-1">1</A> Lindquist N. Fenical W. VanDuyne GD. Clardy J. J. Am. Chem. Soc. 1991, 113: 2303

<A NAME="RT04300SS-2">2</A> Moody CJ. Doyle KJ. Elliot MC. Mowlem TJ. Pure Appl. Chem. 1994, 66: 2107

<A NAME="RT04300SS-3">3</A> Moody CJ. Doyle KJ. Elliott MC. Mowlem TJ. J. Chem. Soc., Perkin Trans. 1 1997, 2413

<A NAME="RT04300SS-4">4</A> Lach F. Moody CJ. Tetrahedron Lett. 2000, 41: 6893

<A NAME="RT04300SS-5">5</A> Bagley MC. Hind SL. Moody CJ. Tetrahedron Lett. 2000, 41: 6897

<A NAME="RT04300SS-6">6</A> Bagley MC. Moody CJ. Pepper AG. Tetrahedron Lett. 2000, 41: 6901

<A NAME="RT04300SS-7">7</A> Konopelski JP. Hottenroth JM. Monzó-Oltra H. Yang Z. Synlett 1996, 609

<A NAME="RT04300SS-8">8</A> Hang HC. Dortleff E. Elliott GI. Konopelski JP. Synthesis 1999, 389

<A NAME="RT04300SS-9">9</A> Wipf P. Yokokawa F. Tetrahedron Lett. 1998, 39: 2223

<A NAME="RT04300SS-10">10</A> Radspieler A. Ziemer B. Liebscher J. Acta Crystallogr., Sect. C 1998, 54: 1351

<A NAME="RT04300SS-11">11</A> Jeong S. Chen X. Harran PG. J. Org. Chem. 1998, 63: 8640

<A NAME="RT04300SS-12">12</A> Chen X. Esser L. Harran PG. Angew. Chem., Int. Ed. 2000, 39: 937

<A NAME="RT04300SS-13">13</A> Boto A. Ling M. Meek G. Pattenden G. Tetrahedron Lett. 1998, 39: 8167

<A NAME="RT04300SS-14">14</A> Magnus P. Kreisberg JD. Tetrahedron Lett. 1999, 40: 451

<A NAME="RT04300SS-15">15</A> Magnus P. McIver EG. Tetrahedron Lett. 2000, 41: 831

<A NAME="RT04300SS-16">16</A> Chan F. Magnus P. McIver EG. Tetrahedron Lett. 2000, 41: 835

<A NAME="RT04300SS-17">17</A> Nicolaou KC. Snyder SA. Somonsen KB. Koumbis AE. Angew. Chem. 2000, 112: 3615

<A NAME="RT04300SS-18">18</A> Vedejs E. Barba DA. Org. Lett. 2000, 2: 1031

<A NAME="RT04300SS-19">19</A> Vedejs E. Barba DA. Org. Lett. 2000, 2: 1033

<A NAME="RT04300SS-20">20</A> Davis M. Lakhan R. Ternai B. J. Heterocycl. Chem. 1977, 14: 317

<A NAME="RT04300SS-21">21</A> Fischer E. Ber. Dtsch. Chem. Ges. 1896, 29: 205

<A NAME="RT04300SS-22">22</A> Rudi A. Stein Z. Green S. Goldberg I. Kashman Y. Benayahu Y. Schleyer M. Tetrahedron Lett. 1994, 35: 2589

<A NAME="RT04300SS-23">23</A> Radspieler A. PhD-thesis Humboldt-University Berlin; Berlin: 2000.

<A NAME="RT04300SS-24">24</A> Adreani A. Bonazzi D. Rambaldi M. Guarnieri A. J. Med. Chem. 1977, 20: 1344

<A NAME="RT04300SS-25">25</A> Olah GA. Arranaghi M. Prakash GK. Synthesis 1983, 636

<A NAME="RT04300SS-26">26</A> Wallace DM. Leung SH. Senge MO. Smith KM. J. Org. Chem. 1993, 58: 7245