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Synlett 2003(3): 0393-0395
DOI: 10.1055/s-2003-37129
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Stereocontrolled Synthesis of Methyl (-)-Nonactate

Joon Won Jeong*a, Byoung Young Wooa, Deok-Chan Hab, Zaesung No*a
a Medicinal Science Division, Korea Research Institute of Chemical Technology, Daejeon 305-343, Korea
Fax: +82(42)8607160; e-Mail: jeongjw@krict.re.kr;
b Department of Chemistry, Korea University, Seoul 136-701, Korea
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Publication History

Received 9 December 2002
Publication Date:
07 February 2003 (online)

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Abstract

A stereoselective synthesis of methyl (-)-nonactate is described. (E)-γ-Triethylsilyloxyalkene 13 generated from sulfone 10 and (S)-2-benzyloxypropanal underwent intramolecular iodo­etherification in the presence of silver carbonate to provide cis-2,5-disubstituted tetrahydrofuran 8 as a key intermediate.

Key words

asymmetric synthesis - cyclizations - sulfones - nonactic acid - iodoetherifications

10

Spectral data for 8: 1H NMR (300 MHz, CDCl3): δ = 7.34-7.22 (5 H, m), 4.59 (1 H, d, J = 11.6 Hz), 4.47 (1 H, d, J = 11.6 Hz), 4.05-3.95 (1 H, m), 3.78-3.72 (2 H, m), 3.70-3.63 (1 H, m), 3.48 (1 H, dd, J = 9.8 Hz, 6.9 Hz), 1.99-1.82 (2 H, m), 1.78-1.42 (5 H, m), 1.24 (3 H, d, J = 6.2 Hz), 0.89 (9 H, s), 0.88 (3 H, d, J = 6.8 Hz), 0.04 (6 H, s); 13C NMR (75 MHz, CDCl3) δ 139.1, 128.3, 127.7, 127.3, 80.5, 76.0, 73.1, 70.7, 65.7, 44.0, 41.3, 31.6, 28.6, 25.9, 20.4, 18.3, 13.1, -5.4; IR (neat) 1251, 1070, 1028, 1006, 834 cm-1; HRMS (EI) calcd for C23H40O5Si: 392.2747, found: 392.2748; [α]D 23 = +23.0, c = 1.00, CHCl3.