Synthesis of the C1-C13 Fragment of (+)-Callipeltoside A

Lucie Boulard; Samir BouzBouz; Jean Marc Paris; Janine Cossy

doi:10.1055/s-2007-980367

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Synlett 2007(9): 1461-1463
DOI: 10.1055/s-2007-980367

LETTER

Synthesis of the C1-C13 Fragment of (+)-Callipeltoside A

Lucie Boulard^a, Samir BouzBouz*^a, Jean Marc Paris^b, Janine Cossy*^a
^a Laboratoire de Chimie Organique, ESPCI, CNRS, 10 Rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(0)140794660; e-Mail: janine.cossy@espci.fr;
^b Laboratoire de Chimie Organique de Synthèse, ENSCP, CNRS, 11 Rue Pierre et Marie Curie, 75230 Paris Cedex 05, France

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Publication History

Received 5 March 2007
Publication Date:
23 May 2007 (online)

Abstract
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Abstract

The synthesis of the C1-C13 fragment of (+)-callipeltoside A has been achieved in 12 steps with an overall yield of 11%.

Key words

callipeltoside - crotyltitanation - vinyllithium

References and Notes

2 Zampella A. D’Auria MV. Minale L. Debitus C. Roussakis C. J. Am. Chem. Soc. 1996, 118: 11085

Crossref Search in Google Scholar
3 Zampella A. D’Auria MV. Minale L. Tetrahedron 1997, 53: 3243

Crossref Search in Google Scholar
4a Paterson I. Davies RD. Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603

Crossref Search in Google Scholar
4b Trost BM. Gunzner JL. J. Am. Chem. Soc. 2001, 123: 9449

Crossref Search in Google Scholar
4c Evans DA. Burch J. Org. Lett. 2001, 3: 503

Crossref Search in Google Scholar
4d Evans DA. Hu E. Burch J. Jaeschke G. J. Am. Chem. Soc. 2002, 124: 5654

Crossref Search in Google Scholar
4e Trost BM. Dirat O. Gunzner JL. Angew. Chem. Int. Ed. 2002, 41: 841

Crossref Search in Google Scholar
4f Trost BM. Gunzner JL. Dirat O. Rhee YH. J. Am. Chem. Soc. 2002, 124: 10396

Crossref Search in Google Scholar
4g Paterson I. Davies RDM. Heimann AC. Marquez R. Meyer A. Org. Lett. 2003, 5: 4477

Crossref Search in Google Scholar
4h Huang H. Panek JS. Org. Lett. 2004, 6: 4383

Crossref Search in Google Scholar
5a Hoye T. Zao H. Org. Lett. 1999, 1: 169

Crossref Search in Google Scholar
5b Velazquez F. Olivo HF. Org. Lett. 2000, 2: 1931

Crossref Search in Google Scholar
5c Olivo HF. Velazquez F. Trevisan HC. Org. Lett. 2000, 2: 4055

Crossref Search in Google Scholar
5d Olivo HF. Romero-Ortega M. Colby DA. Tetrahedron Lett. 2002, 43: 6439

Crossref Search in Google Scholar
6 Hafner A. Duthaler R. Marti R. Rihs G. Streit PR. Schwarzenbach F. J. Am. Chem. Soc. 1992, 114: 2321

Crossref Search in Google Scholar

1

Current address: Laboratoire de Chimie Pharmaceutique, UFR Médecine et Pharmacie, CNRS, 22 Bd Gambetta, 76183 Rouen, France

7

Compound 7: R _f = 0.75 (eluent: hexane-EtOAc, 80:20); [α]_D ²⁰ -3.5 (c 1.0, CHCl₃). IR: 2940, 1750, 1720, 1630, 1470, 1460, 1250, 1090 cm^-1. ¹H NMR: δ = 4.82 (d, J = 9.9 Hz, 1 H), 4.21 (d, J = 5.5 Hz, 1 H), 3.99 (m, 1 H), 3.70-3.52 (m, 6 H), 3.50 (s, 2 H), 3.11 (s, 3 H), 2.80 (dd, J = 15.8, 5.1 Hz, 1 H), 2.72 (dd, J = 15.8, 4.8 Hz, 1 H), 2.22 (t, J = 7.0 Hz, 2 H), 1.69 (m, 1 H), 1.62 (s, 3 H), 1.42 (m, 1 H), 0.87 (d, J = 7.0 Hz, 3 H), 0.86-0.79 (3 s, 27 H), 0.68 (d, J = 6.6 Hz, 3 H), 0.08-0.02 (6 s, 18 H) ppm. ¹³C NMR: δ = 201.2 (s), 167.4 (s), 137.6 (s), 126.5 (d), 78.5 (d), 70.4 (d), 70.1 (d), 62.0 (t), 55.1 (q), 52.0 (q), 50.4 (t), 48.7 (t), 45.2 (d), 43.0 (t), 39.6 (d), 25.9 (3 q), 25.8 (3 q), 25.6 (3 q), 18.2 (s), 18.1 (s), 18.0 (s), 17.1 (q), 11.3 (q), 10.5 (q), -4.0 (q), -4.3 (q), -4.5 (q), -4.6 (q), -4.8 (q), -5.5 (q) ppm.