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DOI: 10.1055/s-2008-1078266
Convergent Synthesis of the A-J Ring System of Yessotoxin
Publikationsverlauf
Publikationsdatum:
21. August 2008 (online)
Abstract
A highly convergent synthesis of the A-J ring system of yessotoxin was achieved. A convergent strategy via α-cyano ethers was extensively applied in the assembly of the F and IJ ring fragments to afford the FGHIJ ring unit, followed by coupling with the ABC ring unit.
Key words
polyether - convergent synthesis - α-cyano ether - ring-closing metathesis - reductive etherification
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References and Notes
The carbon numbering of compounds in this paper corresponds to that of YTX.
22
Physical Data
of 2
[α]D
³0 -10.8
(c 0.04, CHCl3). ¹H
NMR (500 MHz, C6D6): δ = 7.30-6.99
(10 H, m, Ph), 4.41 (1 H, d, J = 12.0
Hz, Bn), 4.37 (1 H, d, J = 12.0
Hz, Bn), 4.33 (1 H, d, J = 12.0
Hz, Bn), 4.18 (1 H, d, J = 12.0
Hz, Bn), 4.00 (1 H, d, J = 2.5
Hz, H32), 3.88 (1 H, ddd, J = 11.5,
10.0, 4.5 Hz, H30), 3.82 (1 H, dd, J = 13.5,
4.0 Hz, H34), 3.72 (1 H, m, H37), 3.65 (1 H, dd, J = 11.0,
4.0 Hz, H38), 3.60 (1 H, dd, J = 11.0,
2.0 Hz, H38), 3.49 (4 H, m, H1, H1, H4, H36), 3.31 (1 H, ddd, J = 10.5, 9.5,
4.0 Hz, H15), 3.27-3.19 (3 H, m, H7, H20, H22), 3.15 (1
H, ddd, J = 9.5,
9.0, 5.5 Hz, H16), 3.12-3.07 (2 H, m, H13, H28), 3.05-3.00
(3 H, m, H9, H10, H31), 2.94-2.88 (2 H, m, H6, H12), 2.64
(1 H, dd, J = 9.5,
9.0 Hz, H27), 2.59 (1 H, ddd, J = 12.0,
4.5, 4.0 Hz, H14), 2.52 (1 H, ddd, J = 10.5, 4.5,
4.0 Hz, H11), 2.42 (1 H, ddd, J = 10.5,
4.5, 4.0 Hz, H29), 2.36-2.29 (2 H, m, H8, H35), 2.20 (1
H, ddd, J = 10.5, 4.0,
4.0 Hz, H5), 2.05-1.98 (2 H, m, H17, H17), 1.91-1.81 (5
H, m, H18, H18, H21, H24, H25), 1.76-1.62 (9 H, m, H2, H2,
H5, H11, H14, H21, H26, H29, H35), 1.60-1.53 (2 H, m, H8,
H24), 1.41 (1 H, dddd, J = 10.0,
9.0, 9.0, 2.5 Hz, H25), 1.27 (3 H, s, Me), 1.26 (3 H, s, Me), 1.16
(3 H, d, J = 6.0
Hz, 26-Me), 1.11 (3 H, s, Me), 1.00 (3 H, s, Me). ¹³C NMR
(150 MHz, C6D6): δ = 139.95,
138.84, 88.61, 86.22, 82.89, 81.83, 81.22, 80.45, 78.97, 78.67,
78.04, 77.82, 77.56 (2 ×), 77.24, 76.86, 75.81, 74.93,
73.43 (3 ×), 73.15, 72.26, 71.62, 71.45, 70.96, 69.80,
69.74, 58.75, 46.50, 43.76, 40.46, 39.87, 39.49, 37.70, 36.21, 35.95,
34.53, 32.74, 32.07, 30.15, 29.78, 23.56, 22.11, 20.59, 14.84, 14.30 (signals
of aromatic region are overlapped with solvent). IR (film): ν = 3437,
2928, 2874, 1453, 1378, 1340, 1286, 1204, 1068, 1025, 738, 698 cm-¹.
HRMS (ESI-TOF): m/z calcd for C57H80O15Na:
1027.5395 [M + Na]+;
found: 1027.5398.