Synthesis and Stereochemical Elucidation of a 14-Membered Ring Phosphonate

Author:

Pungente Michael D.1,Weiler Larry1

Affiliation:

1. Faculty of Pharmaceutical Sciences, University of British Columbia, 2146 East Mall, Vancouver, British Columbia V6T 1Z3, Canada, and Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference14 articles.

1. Total synthesis of the latrunculins

2. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products

3. The synthesis of phosphonate esters; an extension of the Mitsunobu reaction

4. A new stable Wittig reagent suitable for the synthesis of α,β-unsaturated phosphonates

5. Selected data for compounds are as follows.10a: Rf= 0.71 (silica gel, petroleum ether/ethyl acetate 1:1); FTIR (neat) 2927, 2859, 1593, 1490, 1458, 1380, 1253, 1210, 1163, 1071, 991, 920, 766 cm-1;1H NMR (400 MHz, CDCl3) δ 7.05−7.38 (m, 5H), 4.75 (m, 1H), 1.24−1.88 (m, 22H), 1.22 (d,J= 6.3 Hz, 3H);31P NMR (81 MHz, CDCl3) δ 29.6; HRMS calcd for C19H31O3P 338.2011, found 338.2002. Anal. Calcd for C19H31O3P:  C, 67.42; H, 9.24. Found:  C, 67.20; H, 9.20.10b:  mp 97−99 °C.Rf= 0.57 (silica gel, petroleum ether/ethyl acetate 1:1); FTIR (CDCl3) 2932, 2860, 1593, 1492, 1456, 1223, 1011 cm-1;1H NMR (400 MHz, CDCl3) δ 7.05−7.38 (m, 5H), 4.65 (m, 1H), 1.93 (m, 2H), 1.20−1.73 (m, 20H), 1.43 (d,J= 6.2 Hz, 3H);31P NMR (81 MHz, CDCl3) δ 27.8; HRMS calcd for C19H31O3P 338.2011, found 338.2009. Anal. Calcd for C19H31O3P:  C, 67.42; H, 9.24. Found:  C, 67.15; H, 9.39.11:  mp 103−105 °C;Rf= 0.62 (silica gel, petroleum ether/ethyl acetate 1:1); FTIR (CDCl3) 2930, 2856, 1593, 1491, 1229, 1012 cm-1;1H NMR (400 MHz, CDCl3) δ 7.10−7.33 (m, 10H), 4.66 (m, 2H), 1.84 (m, 4H), 1.68 (m, 4H), 1.56 (m, 4H), 1.20−1.45 (m, 40H), 1.15 (d,J= 6.2 Hz, 6H);31P NMR (81 MHz, CDCl3) δ 29.0; HRMS calcd for C38H62O6P2676.4022, found 676.4002. Anal. Calcd for C38H62O6P2:  C, 67.42; H, 9.24. Found:  C, 67.51; H, 9.28.

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