Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E

Hiroyuki Konno; Sachiyo Aoyama; Kazuto Nosaka; Kenichi Akaji

doi:10.1055/s-2007-990848

PAPER

Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E

Hiroyuki Konno*^a, Sachiyo Aoyama^b, Kazuto Nosaka^a, Kenichi Akaji^a
^a Department of Chemistry, Graduate School of Medical Sciences, Kyoto Prefectural University of Medicine, Kita-ku, Kyoto 603-8334, Japan
Fax: +81(75)4657659; e-Mail: konno@koto.kpu-m.ac.jp;
^b Department of Biological Science and Technology, Faculty of Engineering, University of Tokushima, 2-1 Minamijosanjima-cho, Tokushima 770-8506, Japan

Abstract

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Abstract

Asymmetric syntheses of all diastereoisomers of β-methoxytyrosine, an unusual amino acid contained in callipeltin A, were accomplished starting from a cinnamyl ester derivative. The stereochemistry of β-methoxytyrosine in callipeltin E was estimated to be 2R,3R by ¹H and ¹³C NMR analyses of four diastereoisomeric tripeptides, each containing a β-methoxytyrosine isomer. These results obtained from the synthetic peptide derivatives were identical to D’Auria’s results obtained by a degradative procedure.

Key words

callipeltin - cyclodepsipeptide - β-methoxytyrosine - marine sponge - unusual amino acid - anti-HIV activity

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References

<A NAME="RF14207SS-1A">1a</A> Zampella A. D’Auria MV. Gomez-Paloma L. Casapulla A. Debitus C. Henin Y. J. Am. Chem. Soc. 1996, 118: 6202

<A NAME="RF14207SS-1B">1b</A> D’Auria MV. Zampella A. Gomez-Paloma L. Minale L. Tetrahedron 1996, 52: 9589

<A NAME="RF14207SS-1C">1c</A> Zampella A. Randazzo A. Borbone N. Luciani S. Trevisi L. Debitus C. D’Auria MV. Tetrahedron Lett. 2002, 43: 6163

<A NAME="RF14207SS-2A">2a</A> Trevisi L. Bova S. Cargnelli G. Danieli-Betto D. Floreani M. D’Auria MV. Luciani S. Biochem. Biophys. Res. Commun. 2000, 279: 219

<A NAME="RF14207SS-2B">2b</A> Trevisi L. Cargnelli G. Ceolotte G. Papparella I. Semplicini A. Zampella A. D’Auria MV. Luciani S. Biochem. Pharmacol. 2004, 68: 1331

<A NAME="RF14207SS-3A">3a</A> Liang B. Carroll P. Joullié MM. Org. Lett. 2000, 2: 4157

<A NAME="RF14207SS-3B">3b</A> Okamoto N. Hara O. Makino K. Hamada Y. Tetrahedron: Asymmetry 2001, 12: 1353

<A NAME="RF14207SS-3C">3c</A> Acevedo CM. Kogut EF. Lipton MA. Tetrahedron 2001, 57: 6353

<A NAME="RF14207SS-3D">3d</A> Chandrasekhar S. Ramachandar T. Rao BV. Tetrahedron: Asymmetry 2001, 12: 2315

<A NAME="RF14207SS-3E">3e</A> Guerlavais V. Carroll PJ. Joullié MM. Tetrahedron: Asymmetry 2002, 13: 675

<A NAME="RF14207SS-3F">3f</A> Zampella A. Sorgente M. D’Auria MV. Tetrahedron: Asymmetry 2002, 13: 681

<A NAME="RF14207SS-3G">3g</A> Zampella A. D’Auria MV. Tetrahedron: Asymmetry 2002, 13: 1237

<A NAME="RF14207SS-3H">3h</A> Thoen JC. Morales-Ramos AI. Lipton MA. Org. Lett. 2002, 4: 4455

<A NAME="RF14207SS-3I">3i</A> Ravi KA. Venkateswara RB. Tetrahedron Lett. 2003, 44: 5645

<A NAME="RF14207SS-3J">3j</A> Turk JA. Visbal GS. Lipton MA. J. Org. Chem. 2003, 68: 7841

<A NAME="RF14207SS-4">4</A> Okamoto N. Hara O. Makino K. Hamada Y. J. Org. Chem. 2002, 67: 9210

<A NAME="RF14207SS-5">5</A> Hansen DB. Wan X. Carroll PJ. Joullié MM. J. Org. Chem. 2005, 70: 3120

<A NAME="RF14207SS-6">6</A> Zampella A. D’Orsi R. Sepe V. Casapullo A. Monti MC. D’Auria MV. Org. Lett. 2005, 7: 3585

<A NAME="RF14207SS-7">7</A> Calimsiz S. Romos IM. Lipton MA. J. Org. Chem. 2006, 71: 6351

<A NAME="RF14207SS-8">8</A> Krishnamoorthy R. Vazquez-Serrano LD. Tunk JA. Kowalski JA. Benson AG. Breaux NT. Lipton MA. J. Am. Chem. Soc. 2006, 128: 15392

<A NAME="RF14207SS-9A">9a</A> Kolb HC. VanNieuwhenze M. Sharpless KB. Chem. Rev. 1994, 94: 2483

<A NAME="RF14207SS-9B">9b</A> Kwong H. Sorato C. Ogino Y. Chen H. Sharpless KB. Tetrahedron Lett. 1990, 31: 2999

<A NAME="RF14207SS-10A">10a</A> Bodkin JA. McLeod MD. J. Chem. Soc., Perkin Trans. 1 2002, 2733

<A NAME="RF14207SS-10B">10b</A> O’Brien P. Angew. Chem. Int. Ed. 1999, 38: 326

<A NAME="RF14207SS-10C">10c</A> Tao B. Schlingloff G. Sharpless KB. Tetrahedron Lett. 1998, 39: 2507

<A NAME="RF14207SS-10D">10d</A> Li G. Chang H.-T. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996, 35: 451

<A NAME="RF14207SS-11">11</A> O’Brian P. Osborne SA. Parker D. Tetrahedron Lett. 1998, 39: 4099

<A NAME="RF14207SS-12A">12a</A> Cao B. Park H. Joullié MM. J. Am. Chem. Soc. 2002, 124: 520

<A NAME="RF14207SS-12B">12b</A> Park H. Cao B. Joullié MM. J. Org. Chem. 2001, 66: 7223

<A NAME="RF14207SS-13">13</A> Fleming PA. Sharpless KB. J. Org. Chem. 1991, 56: 2869

<A NAME="RF14207SS-14">14</A> Xiong C. Wang W. Hruby V. J. Org. Chem. 2002, 67: 3514

<A NAME="RF14207SS-15">15</A> Carpino LA. Imazumi H. El-Faham A. Ferrer FJ. Zhang C. Lee Y. Foxman BM. Henklein P. Hanay C. Mügge C. Wenschuh H. Klose J. Beyerman M. Bienert M. Angew. Chem. Int. Ed. 2002, 41: 441

<A NAME="RF14207SS-16">16</A> Carpino LA. J. Am. Chem. Soc. 1993, 115: 4397

<A NAME="RF14207SS-17">17</A> Dale JA. Mosher HS. J. Am. Chem. Soc. 1973, 95: 512

<A NAME="RF14207SS-18">18</A> Recently, Cranfill and Lipton reported the synthesis of (2R,3R)-β-MeOTyr using Evans aziridination with chiral bis(oxazoline)copper complex: Cranfill DC. Lipton MA. Org. Lett. 2007, 9: 3511