Angewandte
Chemie
W.H.Yoon, K.C.Fong, H-.S.Choi, Y.He, Y-.L.Zhong, P.S.
approach should provide access to a variety of new analogues
by incorporating different substituents at the periphery.
Applications of the newly developed synthetic strategy and
investigations into the biological activity of wailupemycin B
and its derivatives are currently underway.
Baran, J. Am. Chem. Soc. 2002, 124, 2183 – 2189.
[15] The relative configurations and conformations of various
intermediates were been determined throughout the synthesis
by NOESY experiments.The
rigid precursor to compound 2,
which already contains all ster-
eogenic centers of the natural
Received: March 24, 2003 [Z51455]
product, offered a chance to
check the relative configura-
tion.The most important NOE
data (a = medium, c =
strong) are given in the illus-
Keywords: antibiotics · asymmetric synthesis · ketones ·
polyketides · total synthesis
.
tration
(Ar= 4-methoxy-6-
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[16] Spectroscopic data for 1: 1H NMR (600 MHz, CDCl3, 258C): d =
52, 8073 – 8080.
2
1.62 (d, J = 13.3 Hz, 1H; H8aHb), 2.41 (ddd, 2J = 13.3 Hz, 3J =
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H13aHb), 2.74 (dd, 2J = 18.7 Hz, 3J = 5.3 Hz, 1H; H10aHb), 2.76
2
2
D.M.Hunt, M.S.Newman, B.S.Moore,
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(d, J = 13.6 Hz, 1H; HaH13b), 2.85 (d, J = 14.9 Hz, 1H; H6Hb),
2
2
3.03 (d, J = 14.9 Hz, 1H; HaH6b), 3.14 (br d, J = 18.7 Hz, 1H;
HaH10b), 3.80 (s, 3H; OCH3), 4.01 (br s, 1H; OH), 4.76 (virt. t,
9115 – 9120; e) J.Piel, K.Hoang, B.S.Moore, J. Am. Chem. Soc.
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4
4
3J = 5.0 Hz, 1H; H9), 5.43 (d, J = 2.0 Hz, 1H; H2), 6.02 (d, J =
2.0 Hz, 1H; H4), 7.36–7.41 (m, 3H; CHar), 7.59 ppm (d, 3J =
7.0 Hz, 2H; CHar); 13C NMR (90 MHz, CDCl3, 258C): d = 36.1,
38.7, 43.7, 54.7, 55.8, 69.0, 85.0, 85.4, 88.2, 103.2, 105.9, 125.0,
128.3, 128.9, 138.5, 160.5, 164.3, 171.0, 208.9 ppm; MS (EI,
70 eV): m/z (%): 384 (18) [M+], 356 (48), 209 (51), 140 (100), 125
(50), 105 (92), 77 (33).
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