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Synlett 2012(2): 215-218  
DOI: 10.1055/s-0031-1290097
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of the C1-C13 Fragment of Bistramide A

Loic Tomas, Thibault Bechet, Erwann Jeanneau, David Gueyrard*, Peter G. Goekjian*
Université de Lyon, ICBMS - UMR CNRS 5246, LCO2 - Glycochimie, Université Claude Bernard Lyon 1, Bat. 308 CPE LYON,43, Bd du 11 Novembre 1918, 69622 Villeurbanne, France
Fax: +33(4)72448109; e-Mail: gueyrard@univ-lyon1.fr; e-Mail: goekjian@univ-lyon1.fr;
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Publication History

Received 26 October 2011
Publication Date:
09 December 2011 (online)

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Abstract

Herein we report an efficient synthesis of the C1-C13 fragment of bistramide A from (S)-1,2,4-butanetriol and Roche ester in 14 steps and 13% overall yield.

Key words

bistramide - tetrahydropyran - oxa-Michael - Julia-modified olefination

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9

¹H NMR (300 MHz, CDCl3): δ = 0.82 (d, J = 6.9 Hz, 3 H), 1.32 (m, 2 H), 1.62 (m, 4 H), 2.00 (m, 1 H), 2.20 (dd, J = 2.9, 14.5 Hz, 1 H), 2.87 (dd, J = 12.7, 14.5 Hz, 1 H), 3.78 (m, 1 H), 3.96 (m, 1 H), 4.33 (m, 1 H) ppm. ESI-MS: m/z = 391.2 [M + Na]+. CCDC 843221 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge from The Cambridge Crystallog-raphic Data Centre via http://www.ccdc.ac.uk/data_request/cif.

13

¹H NMR (400 MHz, CDCl3): δ = 0.82 (d, J = 7.0 Hz, 3 H), 1.28 (t, J = 7.2 Hz, 3 H), 1.32-1.39 (m, 1 H), 1.53-1.69 (m, 6 H), 1.93-2.06 (m, 1 H), 2.33 (dd, J = 4.1, 13.5 Hz, 1 H), 2.80 (dd, J = 11.8, 13.5 Hz, 1 H), 2.94-3.01 (m, 1 H), 3.55-3.66 (m, 1 H), 3.68-3.75 (m, 1 H), 3.81-3.91 (m, 1 H), 4.16 (q, J = 7.1 Hz, 2 H), 4.28 (dt, J = 4.9, 4.9, 11.8 Hz, 1 H). ¹³C NMR (100 MHz, CDCl3): δ = 172.9 (C), 74.7 (CH), 68.0 (CH), 61.1 (CH2), 60.2 (CH2), 38.3 (CH2), 33.1 (CH), 32.6 (CH2), 31.8 (CH2), 26.8 (CH2), 17.4 (CH3), 14.2 (CH3). ESI-MS: m/z = 253 [M + Na]+. ESI-HRMS: m/z calcd for C12H22O4Na [M + Na]+: 253.1410; found: 253.1412.