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4.1.10. (E,Z,3RS,5R)-3-(6-Iodohex-5-enyl)-5-methyl-3-
(phenylsulfonyl)-tetrahydrofuran-2-one (4b). This com-
pound was obtained as a yellow oil with 70% yield. H
19.0. HRMS (EI) Calcd for C28H36O5S 484.2283.
Found: 484.2285.
1
NMR (CDCl3, 400 MHz) d: 7.58–7.51 (m, 2H), 7.42–
7.33 (m, 3H), 6.47 (dt, 0.8H, J = 14.4 Hz, 7.2 Hz),
6.20–6.10 (m, 0.4H), 5.97 (dt, 0.8H, J = 14.4 Hz,
1.6 Hz), 4.52–4.43 (m, 1H), 2.56–2.46 (m, 1H), 2.16–
1.91 (m, 3H), 1.81–1.71 (m, 2H), 1.66–1.52 (m, 2H),
1.46–1.31 (m, 2H), 1.21 (d, 3H, J = 6.4 Hz). 13C NMR
(CDCl3, 100 MHz) d: 176.9, 145.9, 137.1 (2C), 130.3,
129.7, 129.0 (2C), 74.6, 74.0, 56.0, 40.2, 36.0, 35.6,
27.8, 23.9, 21.5. HRMS (EI) Calcd for C17H21IO2S
416.0307. Found: 416.0322.
4.1.14. (E,Z,3RS,5R)-3-[(5-Enyl-7-undecaynyl)-11S-hy-
droxy-11-(5S-dihydro-furan-2-onyl)]-5-methyl-3-(phenyl-
sulfonyl)-tetrahydrofuran-2-one (12b). This compound
1
was obtained as a yellow oil with 52% yield. H NMR
(CDCl3, 400 MHz) d: 7.56–7.50 (m, 2H), 7.41–7.31
(m, 3H), 6.01 (dt, 1H, J = 15.6 Hz, 7.2 Hz), 5.42 (dt,
1H, J = 15.6 Hz, 1.6 Hz), 4.49–4.41 (m, 2H), 3.79–
3.71 (m, 1H), 2.62–2.47 (m, 5H), 2.28–2.21 (m, 1H),
2.16–2.05 (m, 4H), 1.98–1.93 (m, 1H), 1.78–1.71 (m,
4H), 1.64–1.55 (m, 1H), 1.40–1.30 (m, 3H), 1.19 (d,
3H, J = 6.4 Hz). 13C NMR (CDCl3, 100 MHz) d:
177.0 (2C), 143.1, 136.8 (2C), 130.3, 129.7, 129.0
(2C), 110.0, 87.3, 82.8, 80.1, 73.2, 72.4, 56.0, 40.1,
36.2, 32.5, 31.7, 28.6 (2C), 24.0 (2C), 21.5, 15.6.
HRMS (EI) Calcd for C26H32O5S 456.1970. Found
456.1961.
4.1.11. (E,Z,3RS,5R)-3-(7-Iodohept-6-enyl)-5-methyl-3-
(phenylsulfonyl)-tetrahydrofuran-2-one (4c). This com-
pound was obtained as a yellow oil with 75% yield.1H
NMR (CDCl3, 400 MHz) d: 7.58–7.50 (m, 2H), 7.42–
7.33 (m, 3H), 6.47 (dt, 0.8H, J = 14.4 Hz, 7.2 Hz),
6.20–6.10 (m, 0.4H), 5.97 (dt, 0.8H, J = 14.4 Hz,
1.6 Hz), 4.52–4.40 (m, 1H), 2.56–2.46 (m, 1H), 2.14–
1.94 (m, 3H), 1.80–1.71 (m, 2H), 1.61–1.50 (m, 2H),
1.43–1.25 (m, 4H), 1.19 (d, 3H, J = 6.4 Hz). 13C NMR
(CDCl3, 100 MHz) d: 176.9, 146.3, 136.8 (2C), 130.3,
129.7, 129.0 (2C), 74.6, 73.2, 56.0, 40.2, 36.3, 35.8,
28.7, 28.0, 24.3, 21.5. HRMS (EI) Calcd for C18H23IO2S
430.0464. Found: 430.0469.
4.1.15.
(E,Z,3RS,5R)-3-[6-Enyl-8-dodecaynyl-12S-hy-
droxy-12-(5S-dihydro-furan-2-onyl)]-5-methyl-3-(phenyl-
sulfonyl)-tetrahydrofuran-2-one (12c). This compound
was obtained as a yellow oil with 57% yield. H NMR
1
(CDCl3, 400 MHz) d: 7.56–7.50 (m, 2H), 7.41–7.31
(m, 3H), 6.00 (dt, 1H, J = 15.6 Hz, 7.2 Hz), 5.40 (dt,
1H, J = 15.6 Hz, 1.6 Hz), 4.49–4.40 (m, 2H), 3.79–3.73
(m, 1H), 2.61–2.54 (m, 1H), 2.49–2.41 (m, 4H), 2.30–
2.21 (m, 1H), 2.18–2.02 (m, 4H), 1.97–1.90 (m, 1H),
1.81–1.68 (m, 4H), 1.61–1.50 (m, 1H), 1.40–1.22 (m,
5H), 1.17 (d, 3H, J = 6.4 Hz). 13C NMR (CDCl3,
100 MHz) d: 177.2, 177.0, 143.5, 136.7 (2C), 130.3,
129.7, 129.0 (2C), 109.7, 87.2, 82.8, 80.1, 73.2, 72.3,
56.1, 40.0, 36.3, 32.6, 31.7, 28.9, 28.6, 28.3, 24.4, 24.0,
21.4, 15.6. HRMS (EI) Calcd for C27H34O5S
470.2127. Found: 470.2120.
4.1.12. (E,Z,3RS,5R)-3-(9-Iodonon-8-enyl)-5-methyl-3-
(phenylsulfonyl)-etrahydrofuran-2-one (4d). This com-
pound was obtained as a yellow oil with 72% yield. H
1
NMR (CDCl3, 400 MHz) d: 7.58–7.50 (m, 2H), 7.42–
7.26 (m, 3H), 6.48 (dt, 0.8H, J = 14.4 Hz, 7.2 Hz),
6.18–6.08 (m, 0.4H), 5.96 (dt, 0.8H, J = 14.4 Hz,
1.6 Hz), 4.52–4.40 (m, 1H), 2.56–2.46 (m, 1H), 2.08–
1.94 (m, 3H), 1.80–1.72 (m, 2H), 1.65–1.52 (m, 2H),
1.41–1.23 (m, 8H), 1.19 (d, 3H, J = 6.0 Hz). 13C NMR
(CDCl3, 100 MHz) d: 176.9, 146.6, 136.8 (2C), 130.4,
129.7, 129.0 (2C), 74.4, 73.2, 56.2, 40.1, 36.5, 36.0,
29.7, 29.4, 28.7, 28.2, 24.6, 21.5. HRMS (EI) Calcd for
C20H27IO2S 458.0776. Found: 458.0779.
4.1.16.
(E,Z,3RS,5R)-3-[6-Enyl-8-tridecaynyl-13S-hy-
droxy-13-(5S-dihydro-furan-2-onyl)]-5-methyl-3-(phenyl-
sulfonyl)-tetrahydrofuran-2-one (12d). This compound
was obtained as a yellow oil with 67% yield. H NMR
1
(CDCl3, 400 MHz) d: 7.55–7.50 (m, 2H), 7.41–7.32
(m, 3H), 6.00 (dt, 1H, J = 15.6 Hz, 7.2 Hz), 5.43 (dt,
1H, J = 15.6 Hz, 1.6 Hz), 4.50–4.39 (m, 2H), 3.63–3.56
(m, 1H), 2.64–2.46 (m, 4H), 2.36–2.30 (m, 2H), 2.29–
2.21 (m, 1H), 2.17–1.85 (m, 4H), 1.78–1.55 (m, 5H),
1.41–1.23 (m, 6H), 1.18 (d, 3H, J = 6.4 Hz). 13C NMR
(CDCl3, 100 MHz) d: 177.0, 176.9, 143.1, 136.7 (2C),
130.3, 129.6, 128.9 (2C), 109.9, 87.8, 83.0, 79.7, 73.2,
73.0, 56.2, 40.1, 36.3, 32.6, 31.9, 28.9, 28.6, 28.4, 24.5,
24.4, 24.0, 21.4, 19.0. HRMS (EI) Calcd for
C28H36O5S 484.2283. Found: 484.2264.
4.1.13.
(E,Z,3RS,5S)-3-[6-Enyl-8-tridecaynyl-13R-hy-
droxy-13-(5R-dihydro-furan-2-onyl)]-5-methyl-3-(phenyl-
sulfonyl)-tetrahydrofuran-2-one (12a). To a solution of
4a (0.22 g, 0.5 mmol) in Et3N (1 mL) under N2 were
added Pd(PPh3)2Cl2 (26 mg, 0.0375 mmol) and CuI
(21 mg, 0.12 mmol). The mixture was stirred at room
temperature for 0.5 h and to it was added a solution
of 3a (0.091 g, 0.5 mmol) in Et3N (1 ml). The reaction
mixture was stirred at room temperature for 24 h and
concentrated. The residue was purified by flash column
chromatography to produce 19a (0.16 g, 65%) as a yel-
1
low oil. H NMR (CDCl3, 400 MHz) d: 7.55–7.50 (m,
4.1.17. (E,Z,3RS,5R)-3-[8-Enyl-10-tetradecaynyl-14S-
hydroxy-14-(5S-dihydro-furan-2-onyl)]-5-methyl-3-(phen-
ylsulfonyl)-tetrahydrofuran-2-one (12e). This compound
2H), 7.38–7.30 (m, 3H), 5.97 (dt, 1H, J = 15.6 Hz,
7.2 Hz), 5.38 (dt, 1H, J = 15.6 Hz, 1.6 Hz), 4.48–4.37
(m, 2 H), 3.60–3.55 (m, 1H), 2.64–2.44 (m, 4H), 2.40–
2.31 (m, 2H), 2.29–2.20 (m, 1H), 2.17–1.85 (m, 4H),
1.78–1.55 (m, 5H), 1.41–1.23 (m, 6H), 1.18 (d, 3H,
J = 6.4 Hz). 13C NMR (CDCl3, 100 MHz) d: 177.3,
177.0, 143.1, 136.6 (2C), 130.2, 129.6, 128.9 (2C),
109.8, 87.8, 83.0, 79.6, 73.2, 73.1, 56.1, 40.0, 36.2,
32.6, 31.7, 28.9, 28.6, 28.4, 24.5, 24.3, 24.0, 21.4,
1
was obtained as a yellow oil with 63% yield. H NMR
(CDCl3, 200 MHz) d: 7.56–7.51 (m, 2H), 7.39–7.28 (m,
3H), 5.99 (dt, 1H, J = 15.6 Hz, 7.2 Hz), 5.45 (dt, 1H,
J = 15.6 Hz, 1.6 Hz), 4.52–4.39 (m, 2H), 3.63–3.52 (m,
1H), 2.63–2.42 (m, 5H), 2.32–1.24 (m, 20H), 1.18 (d,
3H, J = 6.4 Hz). 13C NMR (CDCl3, 50 MHz) d: 177.1
(2C), 143.9, 136.7 (2C), 130.4, 129.7, 129.0 (2C), 109.5,