Synthesis of (2S,3R,4S)-Isonorstatine Using a Solvent-Induced Highly Stereoselective 3-Butenyl Addition to l-Threose Imines

Feng Li; Oliver Schwardt; Volker Jäger

doi:10.1055/s-2006-942426

PAPER

Synthesis of (2S,3R,4S)-Isonorstatine Using a Solvent-Induced Highly Stereoselective 3-Butenyl Addition to l-Threose Imines

Feng Li, Oliver Schwardt, Volker Jäger*
University of Stuttgart, Institut für Organische Chemie, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)68564321; e-Mail: jager.ioc@oc.uni-stuttgart.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

Isonorstatine was obtained in an 11-step sequence starting from l-tartaric acid, based on a highly stereoselective addition of 1-butene-3-yl to a threose imine. The orientation of the methyl group at C-4 of isonorstatine was determined by transformation of the key δ-xylo adduct into a δ-lactone. This also shows that both termini of the key adduct, the diol acetonide and vinyl moiety, can be elaborated selectively into an acid function leading to both aminohydroxymethyl acid and diacid derivatives.

Key words

threose imines - allyl/1-butene-3-yl addition - aminohydroxymethyl acid - solvent effect - N-(1-phenylethyl) auxiliary

Volltext

Referenzen

References

β-Amino acids:

<A NAME="RC03306SS-1A">1a</A> Schmidt U. Kroner M. Griesser H. Synthesis 1989, 832

<A NAME="RC03306SS-1B">1b</A> Juaristi E. Quintana D. Lamatsch B. Seebach D. J. Org. Chem. 1991, 56: 2553

<A NAME="RC03306SS-1C">1c</A> Enantioselective Synthesis of β-Amino Acids Juaristi E. Wiley-VCH; New York: 1977.

<A NAME="RC03306SS-1D">1d</A> Hill DJ. Mio MJ. Prince RB. Hughes TS. Moore JS. Chem. Rev. 2001, 101: 3893

<A NAME="RC03306SS-1E">1e</A> Cheng RP. Gellman SH. DeGrado WF. Chem. Rev. 2001, 101: 3219

<A NAME="RC03306SS-1F">1f</A> Minter AR. Fuller AA. Mapp AK. J. Am. Chem. Soc. 2003, 125: 6846

<A NAME="RC03306SS-1G">1g</A> Zhao YH. Jiang N. Chen SF. Peng C. Zhang XM. Zou YP. Zhang SW. Wang JW. Tetrahedron 2005, 61: 6546

β-Amino hydroxy acids:

<A NAME="RC03306SS-2A">2a</A> Rich DH. In Comprehensive Medicinal Chemistry Vol. 1: Hansh C. Sammes PG. Taylor JB. Pergamon; Oxford: 1990.

<A NAME="RC03306SS-2B">2b</A> Huff JR. J. Med. Chem. 1991, 34: 2305

<A NAME="RC03306SS-2C">2c</A> Thaisrivongs S. Annu. Rep. Med. Chem. 1994, 133

<A NAME="RC03306SS-2D">2d</A> Umezawa H. Aoyagi T. Morishima H. Matzusaki M. Hamada H. Tabeuchi T. J. Antibiot. 1970, 23: 259

<A NAME="RC03306SS-3A">3a</A> Rich DH. Moon BJ. Boparai AS. J. Org. Chem. 1980, 45: 2288

<A NAME="RC03306SS-3B">3b</A> Rich DH. Moon BJ. Harbeson S. J. Med. Chem. 1984, 27: 417

<A NAME="RC03306SS-3C">3c</A> Sugimura H. Miura M. Yamada N. Tetrahedron: Asymmetry 1997, 8: 4089

<A NAME="RC03306SS-4A">4a</A> Iizuka K. Kamijo T. Kubota T. Akahane K. Umeyama H. Kiso Y. J. Med. Chem. 1988, 31: 704

<A NAME="RC03306SS-4B">4b</A> Iizuka K. Kamijo T. Harada H. Akahane K. Kubota T. Umeyama H. Kiso Y. J. Chem. Soc., Chem. Commun. 1989, 1678

<A NAME="RC03306SS-5">5</A> Iizuka K. Kamijo T. Harada H. Akahane K. Kubota T. Etoh Y. Shimaoka I. Tsubaki A. Murakami M. Yamaguchi T. Iyobe A. Umeyama H. Kiso Y. Chem. Pharm. Bull. 1990, 38: 2487

<A NAME="RC03306SS-6">6</A> Iizuka K. Kamijo T. Harada H. Akahane K. Kubota T. Umeyama Ishida T. Kiso Y. J. Med. Chem. 1990, 33: 2707

<A NAME="RC03306SS-7A">7a</A> Jäger V. Wehner V. Angew. Chem., Int. Ed. Engl. 1989, 28: 469

<A NAME="RC03306SS-7B">7b</A> Kieß F.-M. Poggendorf P. Picasso S. Jäger V. Chem. Commun. 1998, 119

<A NAME="RC03306SS-7C">7c</A> Menzel A. Öhrlein R. Griesser H. Jäger V. Synthesis 1999, 1691

<A NAME="RC03306SS-7D">7d</A> Review: Jäger V. Öhrlein R. Wehner V. Poggendorf P. Steuer B. Raczko J. Griesser H. Kieß F.-M. Menzel A. Enantiomer 1999, 4: 205 ; and references cited therein

Reviews:

<A NAME="RC03306SS-8A">8a</A> Risch N. Arend M. In Houben-Weyl, Methoden der Organischen Chemie 4th ed., Vol. E21b: Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1995. p.1833

<A NAME="RC03306SS-8B">8b</A> Enders D. Reinhold U. Tetrahedron: Asymmetry 1997, 8: 1895

<A NAME="RC03306SS-8C">8c</A> Bloch R. Chem. Rev. 1998, 98: 1047

For related additions to ribose imines see:

<A NAME="RC03306SS-8D">8d</A> Lay L. Nicotra F. Paganini A. Pangrazio L. Panza L. Tetrahedron Lett. 1993, 34: 4555

<A NAME="RC03306SS-8E">8e</A> Cippola L. Lay L. Nicotra F. Pangrazio L. Panza L. Tetrahedron 1995, 51: 4679

<A NAME="RC03306SS-8F">8f</A> Kleemann H.-W. Heitsch H. Henning R. Kramer W. Kocher W. Lerch U. Linz W. Nickel W.-U. Ruppert D. Urbach H. Utz R. Wagner A. Weck R. Wiegand F. J. Med. Chem. 1992, 35: 59

<A NAME="RC03306SS-8G">8g</A> Clark RD. . Souchet M. Kern JR. J. Chem. Soc., Chem. Commun. 1989, 930

<A NAME="RC03306SS-9A">9a</A> Franz T. Hein M. Veith U. Jäger V. Peters E.-M. Peters K. von Schnering HG. Angew. Chem., Int. Ed. Engl. 1994, 33: 1298

<A NAME="RC03306SS-9B">9b</A> Veith U. Leurs S. Jäger V. J. Chem. Soc., Chem. Commun. 1996, 329

<A NAME="RC03306SS-10A">10a</A> Veith U. Schwardt O. Jäger V. Synlett 1996, 1181

<A NAME="RC03306SS-10B">10b</A> Schwardt O. Veith U. Gaspard C. Jäger V. Synthesis 1999, 1473

<A NAME="RC03306SS-11">11</A> Meunier N. Veith U. Jäger V. J. Chem. Soc., Chem. Commun. 1996, 331

<A NAME="RC03306SS-12A">12a</A> Steuer B. Wehner V. Lieberknecht A. Jäger V. Org. Synth. 1996, 74: 1

<A NAME="RC03306SS-12B">12b</A> Steuer B. Dissertation Universität Stuttgart; Germany: 1995.

<A NAME="RC03306SS-13A">13a</A> Veith U. Dissertation Universität Stuttgart; Germany: 1995.

<A NAME="RC03306SS-13B">13b</A> Schwardt O. Dissertation Universität Stuttgart; Germany: 1999.

<A NAME="RC03306SS-14A">14a</A> Fujita K. Nakai H. Kobayashi S. Inoue K. Nojima S. Ohno M. Tetrahedron Lett. 1982, 23: 3057

<A NAME="RC03306SS-14B">14b</A> Al-Hakim AH. Haines AH. Morley C. Synthesis 1985, 207

<A NAME="RC03306SS-14C">14c</A> Valverde S. Herradón B. Martin-Lomas M. Tetrahedron Lett. 1985, 26: 3731

<A NAME="RC03306SS-14D">14d</A> Sánchez-Sancho F. Valverde S. Herradón B. Tetrahedron: Asymmetry 1996, 7: 3029

<A NAME="RC03306SS-14E">14e</A> Collins JC. Hess WW. Frank FJ. Tetrahedron Lett. 1968, 3363

<A NAME="RC03306SS-14F">14f</A> Ratcliffe RW. Org. Synth. 1976, 55: 84

<A NAME="RC03306SS-14G">14g</A> Texier-Boullet F. Synthesis 1985, 679

<A NAME="RC03306SS-15">15</A> Krämer B. Franz T. Picasso S. Pruschek P. Jäger V. Synlett 1997, 295

For related allyl additions to both α- and β-alkoxyimines, see:

<A NAME="RC03306SS-16A">16a</A> Yamamoto Y. Komatsu T. Maruyama K. J. Am. Chem. Soc. 1984, 106: 5031

<A NAME="RC03306SS-16B">16b</A> Yamamoto Y. Komatsu T. Maruyama K. J. Org. Chem. 1985, 50: 3115

<A NAME="RC03306SS-16C">16c</A> Yamamoto Y. Komatsu T. Maruyama K. J. Chem. Soc., Chem. Commun. 1985, 814

<A NAME="RC03306SS-16D">16d</A> Yamamoto Y. Ito W. Maruyama K. J. Chem. Soc., Chem. Commun. 1985, 1131

<A NAME="RC03306SS-16E">16e</A> Yamamoto Y. Nishii S. Maruyama K. Komatsu T. Ito W. J. Am. Chem. Soc. 1986, 108: 7778

<A NAME="RC03306SS-16F">16f</A> Yamamoto Y. Ito W. Tetrahedron 1988, 44: 5415

<A NAME="RC03306SS-16G">16g</A> Nakamura H. Iwama H. Yamamoto Y. Chem. Commun. 1996, 1459

<A NAME="RC03306SS-16H">16h</A> Nakamura H. Iwama H. Yamamoto Y. J. Am. Chem. Soc. 1996, 118: 6641

<A NAME="RC03306SS-16I">16i</A> Yamamoto Y. Asao N. Chem. Rev. 1993, 93: 2207

<A NAME="RC03306SS-16J">16j</A> Hoppe D. In Houben-Weyl, Methoden der Organischen Chemie 4th ed., Vol. E21b: Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1995. p.1401

A related strategy has been applied to the synthesis of both enantiomers of goniofufurone from d-glucose where the termini were selectively transformed into allyl alcohol moieties suitable for ensuing oxycarbonylation:

<A NAME="RC03306SS-17A">17a</A> Gracza T. Jäger V. Synlett 1992, 191

<A NAME="RC03306SS-17B">17b</A> Gracza T. Jäger V. Synthesis 1994, 1359

<A NAME="RC03306SS-17C">17c</A> Jäger V. Gracza T. Dubois E. Hasenöhrl T. Hümmer W. Kautz U. Kirschbaum B. Lieberknecht A. Remen L. Shaw D. Stahl U. Stephan O. Proceedings of the Fifth Symposium OSM5 in Organic Synthesis via Organometallics Helmchen G. Vieweg; Braunschweig/Wiesbaden: 1997. p.331

<A NAME="RC03306SS-18A">18a</A> Kraus GA. Roth B. J. Org. Chem. 1980, 45: 4825

<A NAME="RC03306SS-18B">18b</A> Lindgren BO. Hilsson T. Acta Chem. Scand. 1973, 27: 888

For related uses of acetal-protected diols as a latent carboxyl group see, for example, synthesis of furanomycin and its analogues:

<A NAME="RC03306SS-19A">19a</A> Zimmermann PJ. Blanarikova I. Jäger V. Angew. Chem. Int. Ed. 2000, 39: 910

<A NAME="RC03306SS-19B">19b</A> Lee JY. Schiffer G. Jäger V. Org. Lett. 2005, 7: 2317

<A NAME="RC03306SS-19C">19c</A> Zimmermann PJ. Lee JY. Hlobilova I. Endermann R. Häbich D. Jäger V. Eur. J. Org. Chem. 2005, 3450

<A NAME="RC03306SS-19D">19d</A> Henneböhle M. Le Roy P.-Y. Hein M. Ehrler R. Jäger V. Z. Naturforsch., B 2004, 59: 451 ; and references therein

<A NAME="RC03306SS-19E">19e</A> Portolés R. Murga J. Falomir E. Carda M. Uriel S. Marco JA. Synlett 2002, 711

<A NAME="RC03306SS-20">20</A> Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D. Zhang X.-L. J. Org. Chem. 1992, 57: 2768

<A NAME="RC03306SS-21">21</A> Sun XC. Rodriguez M. Zeckner D. Sachs B. Current W. Boyer R. Paschal J. McMillian C. Chen SH. J. Med. Chem. 2001, 44: 2671