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Synlett 2012; 23(12): 1832-1834
DOI: 10.1055/s-0031-1290407
DOI: 10.1055/s-0031-1290407
letter
Asymmetric Total Synthesis of ent-Tetrahydrolipstatin from an Epoxy Alkenol
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Further Information
Publication History
Received: 12 April 2012
Accepted after revision: 07 May 2012
Publication Date:
04 July 2012 (online)
Abstract
A highly efficient asymmetric total synthesis of ent-tetrahydrolipstatin (THL) was accomplished from the known epoxy alkenol. The β-lactone portion of THL was synthesized by the epoxide opening with cyanide and stereoselective enolate alkylation method. The side chain was introduced by cross metathesis of the alkene part with 1-decene. Coupling with a protected leucine completed the synthesis of ent-tetrahydrolipstatin.
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- 14 Spectral Data for ent-Tetrahydrolipstatin (1) Rf = 0.32 (silica gel, hexane–EtOAc = 7:3); [α]D 20 +30.66 (c 0.36, CHCl3); mp 41–42 °C. 1H NMR (400 MHz, CDCl3): δ = 8.22 (s, 1 H), 5.93 (d, J = 8.0 Hz, 1 H), 5.04–5.02 (m, 1 H), 4.71–4.67 (m, 1 H), 4.31–4.27 (m, 1 H), 3.23–3.21 (m, 1 H), 2.19–2.15 (m, 1 H), 2.03–1.98 (m, 1 H), 1.87–1.54 (m, 7 H), 1.29–1.25 (m, 26 H), 0.98–0.94 (m. 6 H), 0.90–0.86 (m, 6 H). 13C NMR (100.6 MHz, CDCl3): δ = 172.1, 170.9, 160.8, 74.9, 72.9, 57.2, 49.8, 41.7, 38.9, 34.2, 32.1, 31.6, 29.8, 29.7, 29.6, 29.5, 29.1, 27.8, 26.9, 25.2, 25.1, 23.0, 22.8, 22.7, 21.9, 14.3, 14.2. IR (film): 3353, 3025, 2954, 2924, 2855, 1825, 1733, 1699, 1652, 1521, 1456, 1386, 1273, 1250, 1195, 1126, 877, 815, 761 cm–1. HRMS: m/z calcd for C29H54NO5[M + H]+: 496.4002; found: 496.4004