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Beilstein J. Org. Chem. 2014, 10, 2077–2086, doi:10.3762/bjoc.10.216
Graphical Abstract
Figure 1: Examples of naturally occurring tetrahydrofurans.
Scheme 1: PdCl2/CuCl2-catalysed bicyclisation of unsaturated polyols [22].
Figure 2: Structures of C5-alkenitols.
Scheme 2: Synthesis of alkenols 20-23 and 30. Reagents and conditions: a) lit. [31] (COCl)2, DMSO, Et3N, CH2Cl2, ...
Scheme 3: Synthesis of alkenols 24–26 and 28. Reagents and conditions: a) lit. [32] DIBAL-H, CH2Cl2; b) TBDPSCl, ...
Scheme 4: Synthesis of substrates 33–35, 37. Reagents and conditions: a) lit. [33] L-proline (0.25 equiv), 2-nitr...
Scheme 5: Synthesis of rac-42. Reagents and conditions: a) MCPBA, CH2Cl2, 0 °C to rt, 45 min; b) TFA, H2O, TH...
Figure 3: Structure of 43.
Scheme 6: Suggested mechanisms for PdII–Pd0, PdII–PdIV and PdII-chloro/cyclisation of unsaturated polyols.
Figure 4: An ORTEP [44] view of crystal and molecular structure of 53.
Scheme 7: Bicyclisation of 55–58. Reagents and conditions: a) NaH, DMF, 50 °C, 2 h; b) I2, CH3CN, rt, overnig...