Y. Kita et al.
FULL PAPER
diastereomer), 4.58 (m, 1H, overlap with signals of the other diastereo-
mer), 2.68 (m, 1H, overlap with signals of the other diastereomer), 2.33 (s,
3H, m, 1H, overlap with signals of the other diastereomer), 2.31 0.84 (m,
28H, overlap with signals of the other diastereomer), 2.04 (s, 3H, overlap
with signals of the other diastereomer), 1.00 (s, 3H), 0.48 (s, 3H).
80.24, H 8.51; found: C 79.90, H 8.70; X-ray data: see the Supporting
Information.
(1R,2S)-4 f: Colourless crystals; m.p. 180 1818C (Et2O/hexane); 1H NM R
(270 MHz, CDCl3): d 7.73 7.81 (m, 3H), 7.64 (s, 1H), 7.33 7.44 (m, 3H),
5.34 (m, 1H), 5.09 (m, 1H), 4.55 (m, 1H), 2.86 (m, 1H), 2.27 (m, 2H), 2.03
(s, 3H), 0.98 (s, 3H), 0.66 2.23 (m, 26H), 0.43 (s, 3H); IR (KBr): nÄ
Mixture of compounds 3c and 4c:
1727 cmÀ1
.
(1S,2R)-3c: Colourless crystals: m.p. 176 176.58C (Et2O/hexane);
1H NMR (270 MHz, CDCl3): d 7.11 (d, J 8.6 Hz, 2H), 6.80 (d, J
8.6 Hz, 2H), 5.34 (m, 1H), 4.98 (m, 1H), 4.60 (m, 1H), 3.76 (s, 3H), 2.64
(m, 1H), 2.30 (m, 2H), 2.03 (s, 3H), 0.95 (s, 3H), 0.85 2.18 (m, 26H), 0.006
(s, 3H); IR (KBr): nÄ 1715 cmÀ1; elemental analysis calcd (%) for
C35H48O5 (548.8): C 76.61, H 8.82, found: C 76.30, H 8.60; X-ray data:
see the Supporting Information.
Mixture of compounds 3g and 4g:
(1S*,2R*)-3g: Colourless crystals; m.p. 126.0 129.08C (Et2O/hexane);
1
[a]2D8 22.3 (c 0.63, CHCl3); H NMR (300 MHz, CDCl3): d 8.52 (d,
J 4.5 Hz, 1H), 7.57 (td, J 7.7, 1.8 Hz, 1H), 7.18 (d, J 7.7 Hz, 1H), 7.09
(ddd, J 7.7, 4.5, 0.8 Hz, 1H), 5.33 (d, J 4.2 Hz, 1H), 5.24 (td, J 10.8,
4.3 Hz, 1H), 4.58 (m, 1H), 2.91 (td, J 11.5, 3.5 Hz, 1H), 2.31 0.84 (m,
28H), 2.03 (s, 3H), 0.95 (s, 3H), 0.11 (s, 3H); IR (KBr): nÄ 1732 cmÀ1; M S
(1R,2S)-4c: Colourless crystals; m.p. 153 1548C (Et2O/hexane); 1H NM R
(270 MHz, CDCl3): d 7.11 (d, J 8.6 Hz, 2H), 6.80 (d, J 8.6 Hz, 2H),
5.38 (m, 1H), 4.87 (m, 1H), 4.60 (m, 1H), 3.77 (s, 3H), 2.61 (m, 1H), 2.32
(m, 2H), 2.03 (s, 3H), 1.00 (s, 3H), 0.97 2.18 (m, 26H), 0.490 (s, 3H); IR
(KBr): nÄ 1732 cmÀ1; X-ray data: see the Supporting Information.
EI(); m/z (%): 519 (3) [M] , 160 (100); HRMS calcd for C33H45NO4:
519.3348 [M] ; found: 519.3367; elemental analysis calcd (%) for
C33H45NO4 (519.7): C 76.26, H 8.73, N 2.70; found: C 76.06, H 8.72, N 2.62.
(1R*,2S*)-4g: Colourless crystals; m.p. 149.5 150.08C (Et2O/hexane);
1
[a]2D8 À70.7 (c 0.59, CHCl3); H NMR (300 MHz, CDCl3): d 8.51 (d,
Mixture of compounds 3d and 4d: Colourless solid; m.p. 59 608C; IR
J 4.4 Hz, 1H), 7.56 (td, J 7.7, 1.8 Hz, 1H), 7.13 (d, J 7.7 Hz, 1H), 7.09
(ddd, J 7.7, 4.4, 0.9 Hz, 1H), 5.34 (d, J 4.4 Hz, 1H), 5.13 (td, J 11.0,
4.2 Hz, 1H), 4.59 (m, 1H), 2.88 (td, J 11.0, 3.6 Hz, 1H), 2.32 0.88 (m,
28H), 2.03 (s, 3H), 0.99 (s, 3H), 0.46 (s, 3H); IR (KBr): nÄ 1732 cmÀ1; M S
(KBr): nÄ 1728 cmÀ1
;
HRMS calcd for C34H45O4Cl: 552.3007 [M] ;
found:552.3014 .
(1S*,2R*)-3d: 1H NMR (270 MHz, CDCl3): d 7.24 (d, J 8.6 Hz, 2H,
overlap with signals of the other diastereomer), 7.16 (d, J 8.6 Hz, 2H,
overlap with signals of the other diastereomer), 5.34 (m, 1H, overlap with
signals of the other diastereomer), 4.98 (m, 1H, overlap with signals of the
other diastereomer), 4.61 (m, 1H, overlap with signals of the other
diastereomer), 2.68 (m, 1H, overlap with signals of the other diastereo-
mer), 2.32 (m, 2H, overlap with signals of the other diastereomer), 2.29
0.81 (m, 26H, overlap with signals of the other diastereomer), 2.04 (s, 3H,
overlap with signals of the other diastereomer), 0.97 (s, 3H), 0.12 (s, 3H).
EI(); m/z (%): 520 (1) [MH] , 519 (1) [M] , 459 (100); HRMS calcd for
C33H45NO4: 519.3348 [M] ; found: 519.3358; elemental analysis calcd (%)
for C33H45NO4 (519.7): C 76.26, H 8.73, N 2.70; found: C 75.96, H 8.62, N
2.70.
Mixture of compounds 3h and 4h: Colourless solid; m.p. 107.0 112.58C;
IR (KBr): nÄ 1730 cmÀ1; HRMS calcd for C34H47NO4: 533.3505 [M] ;
found: 533.3529.
(1S*,2R*)-3h: 1H NMR (300 MHz, CDCl3): d 8.39 (d, J 4.6 Hz, 1H,
overlap with signals of the other diastereomer), 7.36 (d, J 7.6 Hz, 1H,
overlap with signals of the other diastereomer), 6.97 (dd, J 7.6, 4.6 Hz,
1H, overlap with signals of the other diastereomer), 5.43 5.30 (m, 2H),
4.59 (m, 1H, overlap with signals of the other diastereomer), 3.10 (td, J
10.8, 4.0 Hz, 1H), 2.43 0.75 (m, 28H, overlap with signals of the other
diastereomer), 2.35 (s, 3H), 2.03 (s, 3H, overlap with signals of the other
diastereomer), 0.94 (s, 3H), 0.13 (s, 3H).
(1R*,2S*)-4h: 1H NMR (300 MHz, CDCl3): d 8.39 (d, J 4.6 Hz, 1H,
overlap with signals of the other diastereomer), 7.36 (d, J 7.6 Hz, 1H,
overlap with signals of the other diastereomer), 6.97 (dd, J 7.6, 4.6 Hz,
1H, overlap with signals of the other diastereomer), 5.33 (d, J 5.0 Hz,
1H), 5.20 (td, J 10.5, 4.0 Hz, 1H), 4.59 (m, 1H, overlap with signals of the
other diastereomer), 3.10 (td, J 10.8, 4.0 Hz, 1H), 2.43 0.75 (m, 28H,
overlap with signals of the other diastereomer), 2.36 (s, 3H), 2.03 (s, 3H,
overlap with signals of the other diastereomer), 0.99 (s, 3H), 0.44 (s, 3H).
(1R*,2S*)-4d: 1H NMR (270 MHz, CDCl3): d 7.24 (d, J 8.6 Hz, 2H,
overlap with signals of the other diastereomer), 7.16 (d, J 8.6 Hz, 2H,
overlap with signals of the other diastereomer), 5.34 (m, 1H, overlap with
signals of the other diastereomer), 4.98 (m, 1H, overlap with signals of the
other diastereomer), 4.61 (m, 1H, overlap with signals of the other
diastereomer), 2.68 (m, 1H, overlap with signals of the other diastereo-
mer), 2.32 (m, 2H), 0.81 2.29 (m, 26H, overlap with signals of the other
diastereomer), 2.04 (s, 3H, overlap with signals of the other diastereomer),
1.00 (s, 3H), 0.49 (s, 3H).
Mixture of compounds 3e and 4e: Colourless solid; m.p. 139 1408C; IR
(KBr): nÄ 1736 cmÀ1; HRMS calcd for C38H48O4: 568.3553 [M] ; found:
568.3559.
(1S*,2R*)-3e: 1H NMR (270 MHz, CDCl3): d 8.18 (d, J 8.6 Hz, 1H,
overlap with signals of the other diastereomer), 7.81 (d, J 8.2 Hz, 1H,
overlap with signals of the other diastereomer), 7.51 (d, J 7.9 Hz, 1H),
7.40 7.48 (m, 4H, overlap with signals of the other diastereomer), 5.26
5.30 (m, 1H, overlap with signals of the other diastereomer), 5.18 5.26 (m,
1H, overlap with signals of the other diastereomer), 4.58 (m, 1H, overlap
with signals of the other diastereomer), 3.64 (m, 1H, overlap with signals of
the other diastereomer), 2.27 (m, 2H, overlap with signals of the other
diastereomer), 2.02 (s, 3H), 0.37 1.98 (m, 26H, overlap with signals of the
other diastereomer), 0.83 (s, 3H), À0.21 (s, 3H).
Mixture of compounds 3i and 4i:
(1S,2R)-3i: Colourless crystals; m.p. 199.0 202.08C (AcOEt/hexane);
1
[a]2D9 19.2 (c 0.51, CHCl3); H NMR (300 MHz, CDCl3): d 8.37 (d,
J 5.0 Hz, 1H), 6.99 (s, 1H), 6.91 (d, J 5.0 Hz, 1H), 5.33 (d, J 4.4 Hz,
1H), 5.22 (td, J 10.7, 4.3 Hz, 1H), 4.58 (m, 1H), 2.86 (td, J 11.4, 3.4 Hz,
1H), 2.30 0.84 (m, 28H), 2.30 (s, 3H), 2.03 (s, 3H), 0.95 (s, 3H), 0.10 (s,
3H); IR (KBr): nÄ 1732, 1721 cmÀ1; MS EI(); m/z (%): 533 (10) [M] ,
(1R*,2S*)-4e: 1H NMR (270 MHz, CDCl3): d 8.18 (d, J 8.6 Hz, 1H,
overlap with signals of the other diastereomer), 7.81 (d, J 8.2 Hz, 1H,
overlap with signals of the other diastereomer), 7.51 (d, J 7.9 Hz, 1H),
7.40 7.48 (m, 4H, overlap with signals of the other diastereomer), 5.26
5.30 (m, 1H, overlap with signals of the other diastereomer), 5.18 5.26 (m,
1H, overlap with signals of the other diastereomer), 4.58 (m, 1H, overlap
with signals of the other diastereomer), 3.64 (m, 1H, overlap with signals of
the other diastereomer), 2.27 (m, 2H, overlap with signals of the other
diastereomer), 2.04 (s, 3H), 0.37 1.98 (m, 26H, overlap with signals of the
other diastereomer), 0.97 (s, 3H), 0.32 (s, 3H).
473 (100); HRMS calcd for C34H47NO4: 533.3505 [M] ; found: 533.3499;
elemental analysis calcd (%) for C34H47NO4 (533.8): C 76.51, H 8.88, N 2.62;
found: C 76.33, H 8.74, N 2.62; X-ray data: see the Supporting Information.
(1R,2S)-4i: Colourless crystals; m.p. 149.0 151.08C (AcOEt/hexane);
1H NMR (300 MHz, CDCl3): d 8.36 (d, J 4.7 Hz, 1H), 6.94 (s, 1H), 6.90
(d, J 4.7 Hz, 1H), 5.35 (d, J 4.8 Hz, 1H), 5.11 (td, J 10.3, 4.3 Hz, 1H),
4.59 (m, 1H), 2.84 (td, J 11.4, 3.3 Hz, 1H), 2.30 (s, 3H), 2.21 0.88 (m,
28H), 2.03 (s, 3H), 1.00 (s, 3H), 0.46 (s, 3H); IR (KBr): nÄ 1732 cmÀ1; M S
EI(); m/z (%): 533 (4) [M] , 473 (100); HRMS calcd for C34H47NO4:
533.3505 [M] ; found: 533.3527; elemental analysis calcd (%) for
C34H47NO4 (533.8): C 76.51, H 8.88, N 2.62; found: C 76.33, H 8.87, N 2.58.
Mixture of compounds 3 f and 4 f:
Mixture of compounds 3j and 4j: Colourless solid; m.p. 112.0 118.58C; IR
(1S,2R)-3 f: Colourless crystals; m.p. 198 199.58C (Et2O/hexane);
1H NMR (270 MHz, CDCl3): d 7.73 7.81 (m, 3H), 7.62 (s, 1H), 7.33
7.44 (m, 3H), 5.26 (m, 1H), 5.09 (m, 1H), 4.55 (m, 1H), 2.86 (m, 1H), 2.27
(m, 2H), 1.97 (s, 3H), 0.66 2.23 (m, 26H), 0.69 (s, 3H), À0.25 (s, 3H); IR
(KBr): nÄ 1720 cmÀ1; elemental analysis calcd (%) for C38H48O4 (568.8): C
(KBr): nÄ 1728 cmÀ1; HRMS calcd for C34H47NO4: 533.3505 [M] ; found:
533.3507.
(1S*,2R*)-3j: 1H NMR (300 MHz, CDCl3): d 8.35 (d, J 2.2 Hz, 1H),
7.38 (dd, J 8.1 and 2.2 Hz, 1H), 7.07 (d, J 8.1 Hz, 1H), 5.33 (d,
5560
¹ 2002 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
0947-6539/02/0824-5560 $ 20.00+.50/0
Chem. Eur. J. 2002, 8, No. 24