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

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

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

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

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References and Notes

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

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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.