Electronic Supporting Information. General Experimental Details. Jack Li-Yang Chen and Margaret A. Brimble*
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1 Electronic Supporting Information Synthesis of the Bis-spiroacetal C 2 C 40 Moiety of the Antimitotic Agent Spirastrellolide B using a Bis-dithiane Deprotection / Spiroacetalisation Sequence Jack Li-Yang Chen and Margaret A. Brimble* Department of Chemistry, University of Auckland, 2 Symonds Street, Auckland, New Zealand. m.brimble@auckland.ac.nz General Experimental Details Thin-layer chromatography (TLC) was carried out using E. Merck silica gel plates using UV light as the visualising agent and/or developed using an ethanolic solution of vanillin or ammonium molybdate and cerium sulfate in aqueous sulfuric acid. ptical rotations were measured with a Perkin Elmer 41 polarimeter, using the sodium-d line (89 nm), with the concentration of the solution measured in grams per 100 ml. Infrared (IR) spectra were recorded using a Perkin Elmer Spectrum 1000 FT-IR spectrometer with the absorption peaks expressed in wavenumbers (cm -1 ) and recorded using a range of 40 to 4000 cm -1. NMR spectra were recorded in CDCl or C 6 D 6 on either a Bruker BRX00 spectrometer operating at 00 Mz for 1 nuclei and 7 Mz for 1 C nuclei or a Bruker DRX400 spectrometer operating at 400 Mz for 1 nuclei and 100 Mz for 1 C nuclei. Chemical shifts are reported as parts per million (ppm) from tetramethylsilane ( = 0) and were measured relative to the solvent in which the sample was analysed (CDCl : 7.26 for 1 NMR, 77.0 for 1 C NMR and C 6 D 6 : 7.1 for 1 NMR, for 1 C NMR) and coupling constants (J) are reported in hertz (z) to the nearest 0.1 ppm. 1 NMR data is reported as chemical shift in ppm, followed by relative integral, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublets, m = multiplet, br = broad) and coupling constants where applicable. igh resolution mass spectra were recorded using a VG70-SE spectrometer or on a micrtf-q mass spectrometer. 1
2 Characterisation Data (S)-2-(4-(tert-Butyldimethylsilyloxy)butan-2-yl)-1,-dithiane (10) Me TBS R f (hexanes/etac :1) = 0.6; [ ] D (c 1.7 in CCl ); IR ν max (film)/cm , 2929, 289, 286, 1471, 1462, 12, 109, 8, 774; 1 NMR (00 Mz, CDCl ): 4.1 (1, d, J = 4.0 z),.70.6 (2, m, 4-), (4, m), (2, m), (2, m), 1.49 (1, ddt, J = 1.7, 8.4,.7 z), 1.06 (, d, J = 7.0 z), 0.86 (9, s), 0.0 (, s), 0.0 (, s); 1 C NMR (7 Mz, CDCl ): C 61.0,.6, 6.8,.1, 1.1, 0.8, 26.4, 2.9, 18., 16.9,.; RMS Found (EI): M , C 14 0 S 2 Si requires (2S,S)-1,2-Epoxy--(ethoxymethoxy)--(4-methoxybenzyloxy)pentane (8) 4 EM 2 1 R f (hexanes/etac :1) = 0.24; [ ] D (c 0.64 in CCl ); IR ν max (film)/cm , 2929, 2869, 1612, 11, 1246, 117, 1094, 1028, 846, 816; 1 NMR (00 Mz, CDCl ): 7.24 (2, d, J = 8.6 z), 6.87 (2, d, J = 8.6 z), 4.86 (1, d, J = 6.8 z), 4.72 (1, d, J = 6.8 z), 4.64 (1, d, J = 11.6 z), 4.40 (1, d, J = 11.6 z),.80 (, s),.66.4 (4, m),.49 (1, q, J = 6.7 z),.00 (1, ddd, J = 6.7, 4., 2.8 z), 2.7 (1, dd, J = 4.8, 4. z), 2.2 (1, dd, J = 4.8, 2.8 z), (2, m), 1.20 (, t, J = 7.1 z); 1 C NMR (7 Mz, CDCl ): C 19.2, 10., 129.2, 11.7, 94., 7., 72.7, 6.9, 6.,.2, 4.6, 4.7, 2., 1.0; RMS Found (ESI): (M + Na) +, , C Na requires
3 (S)-1-(tert-Butyldimethylsilyloxy)--(2-((2 S, S)- -(ethoxymethoxy)-2 -hydroxy- -(4- methoxybenzyloxy)-pentan-1 -yl)-1,-dithian-2-yl)butane (11) EM 4 Me 1 TBS R f (hexanes/etac :1) = 0.19; [ ] D (c 0.40 in CCl ); IR ν max (film)/cm , 2927, 2900, 2864, 1611, 11, 146, 18, 1247, 1087, 100, 90, 82, 774, 619; 1 NMR (00 Mz, CDCl ): 7.26 (2, d, J = 8.6 z), 6.87 (2, d, J = 8.6 z), 4.7 (1, d, J = 7.0 z), 4.70 (1, d, J = 7.0 z), 4.44 (2, s), (1, m),.80 (, s),.76.1 (7, m),.2 (1, d, J =.9 z), (4, m), 2.40 (1, dqd, J = 10.4, 6.7, 2.0 z), (1, m), (, m), (2, m), 1.81 (1, dddd, J = 14.1, 7.9,.7,.7 z), (1, m), 1.20 (, t, J = 7.1 z), 1.1 (, d, J = 6.8 z), 0.90 (9, s), 0.06 (, s), 0.0 (, s); 1 C NMR (7 Mz, CDCl ): C 19.1, 10.4, 129., 11.7, 94.9, 78.6, 72.6, 69.2, 66.7, 6.7, 61.6, 8.,.2, 7.6,.0, 4.6, 0.7, 2.9, 2.7, 24.8, 18., 1.0, 14.6,.4; RMS Found (ESI): M +, 60.19, C 0 6 S 2 Si requires (S)--(2-((2 S, S)-2 -(Benzyloxy)- -(ethoxymethoxy)- -(4-methoxybenzyloxy)-pentan-1 -yl)- 1,-dithian-2-yl)butanal (1) EM Bn 4 Me 1 R f (hexanes/etac 2:1) = 0.; [ ] D (c 0.8 in CCl ); IR ν max (film)/cm , 2889, 2860, 1720, 1612, 11, 14, 172, 124, 1179, 109, 100, 819, 77, 699; 1 NMR (400 Mz, CDCl ): 9.7 (1, d, J = 2.0 z), (7, m), 6.87 (2, d, J = 8.6 z), 4.7 (1, d, J = 7.0 z), 4.66 (1, d, J = 7.0 z), 4.62 (1, d, J = 10.8 z), 4.8 (1, d, J = 10.8 z), 4.4 (2, s), (2, m),.80 (, s),.66. (4, m),.24 (1, dd, J = 17.6,. z), (, m), 2.40 (1, ddd, J = 17.6, 8.8, 2.0 z), 2.1 (1, br d, J = 1. z), (4, m), 1.68 (1, ddt, J = 14., 9.0,. z), 1.22 (, t, J = 7.0 z), 1.11 (, d, J = 6.7 z); 1 C NMR (100 Mz, CDCl ): C 201., 19.1, 18., 10.6, 129.2, 128.2, 128.2, 127., 11.7, 94.4, 76.9, 72.6, 72., 71.7, 67.0, 6.6, 8.1,., 47.7, 4., 4.0, 29.6, 2.8, 2., 2.0, 1.7, 1.1; RMS Found (ESI): M +, , C S 2 requires
4 (2S,4S)-1-(tert-Butyldiphenylsilyloxy)--(1,-dithian-2-yl)-2-(ethoxymethoxy)-4-methoxypentane (6) Me EM TBDPS R f (hexanes/etac :1) = 0.4; [ ] D 19 = 19. (c 1.28 in CCl ); IR ν max (film)/cm , 2890, 287, 1471, 1427, 189, 1076, 1028, 822, 790, 79, 700, 61, 2, 18; 1 NMR (00 Mz, CDCl ): (4, m), (6, m), 4.81 (1, d, J = 6.8 z), 4.72 (1, d, J = 6.8 z), 4.1 (1, dd, J = 7.8, 6.1 z), (1, m),.7.49 (, m),.7 (, s), (4, m), (1, m), (4, m), (1, m), 1.1 (, t, J = 7.1), 1.0 (9, s); 1 C NMR (7 Mz, CDCl ): C 1.6, 1.4, 129.6, 127.6, 9.2, 7., 74.2, 66.7, 6.4, 6., 4.6, 40.2, 7.2, 0.4, 0., 26.8, 2.9, 19.2, 1.0; RMS Found (EI): M +, 48.24, C S 2 Si requires (1S,S)--(2-((2 S, S)-2 -(Benzyloxy)- -(ethoxymethoxy)- -(4-methoxybenzyloxy)-pentan-1 - yl)-1,-dithian-2-yl)-1-(2-((2 S,4 S)- -(tert-butyldiphenylsilyloxy)-4 -(ethoxymethoxy)-2 - methoxypentan-1 -yl)-1,-dithian-2-yl)butan-1-ol (17a) EM 4Me 1 Bn TBDPS Me EM R f (hexanes/etac :1) = 0.26; [ ] D (c 0.67 in CCl ); IR ν max (film)/cm , 2900, 286, 1612w, 11, 1460, 1427, 190, 1247, 1178, 1102, 109, 101, 82, 72, 701, 612; 1 NMR (00 Mz, CDCl ): (4, m), (1, m), 6.8 (2, d, J = 8.6 z), 4.8 (1, d, J = 6.9 z), 4.76 (1, d, J = 7.0 z), 4.76 (1, d, J = 7.0 z), 4.66 (1, d, J = 7.0 z), 4.6 (1, d, J = 10.9 z), 4.7 (1, d, J = 10.9 z), 4.42 (2, s), (, m), (, m),.74.2 (8, m),.6 (, s), (9, m), (2, m), (4, m), (8, m), 1.20 (, t, J = 7.0 z), 1.17 (, t, J = 7.0 z), 1.1 (, d, J = 7.0 z), 1.0 (9, s); 1 C NMR (7 Mz, CDCl ): C 19.1, 18.8, 1.7, 1., 10.8, 129.6, 129.2, 128.1, 127.6, 127., 11.7, 9.2, 94., 77.2, 76.1, 7.1, 72.9, 72.4, 71.7, 70.8, 67.2, 66.8, 6.6, 6.4, 9.2, 8.4, 6.1,., 9.8, 9.1, 6., 4.6,., 29.7, 26.9, 26.0, 2.6, 2., 2.2, 24.4, 19.2, 1.1, 14.8; RMS Found (ESI): (M + Na) +, , C Na 10 S 4 Si requires
5 (1S,S)--(2-((2 S, S)-2 -(Benzyloxy)- -hydroxy- -(4-methoxybenzyloxy)-pentan-1 -yl)-1,- dithian-2-yl)-1-(2-((2 S,4 S)- -(tert-butyldiphenylsilyloxy)-4 -hydroxy-2 -methoxypentan-1 - yl)-1,-dithian-2-yl)-butan-1-ol Bn 4Me 1 Me TBDPS R f (hexanes/etac 2:1) = 0.1; [ ] D (c 0.8 in CCl ); IR ν max (film)/cm , 2926, 287, 17w, 1612w, 11, 14, 1427, 178, 1248, 1076br, 107, 908, 822, 77, 701, 670, 608; 1 NMR (00 Mz, CDCl ): (4, m), (1, m), 6.86 (2, d, J = 8.6 z), 4.76 (1, d, J = 10.9 z), 4.4 (1, d, J = 11.4 z), 4.4 (2, s), (, m),.80 (, s),.7.2 (4, m),.6 (, s),.24 (1, br s),.0 (1, br s), (8, m), (1, m), 2. (1, br d, J = 1.2 z), (, m), (9, m), 1.24 (, d, J = 6.7 z), 1.07 (9, s); 1 C NMR (7 Mz, CDCl ): C 19.2, 18.9, 1.6, 1., 10.2, 129.7, 129., 128.2, 127.9, 127.7, 127.4, 11.8, 78.9, 77.2, 72.9, 72., 71.8, 71.7, 69.6, 69.1, 68.2, 8.6, 8.2, 6.6,.2, 40.7, 8., 6.1,.,.0, 1., 26.9, 26.1, 2.8, 2.6, 2., 2.1, 24., 19., 1.1; RMS Found (ESI): (M + Na) +, , C 4 76 Na 8 S 4 Si requires (2S,S,R,7S,9S,11S,1S,1S)--(Benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1 -(4- methoxybenzyloxy)ethan-2 -yl)-1-hydroxy-11-methoxy-1-methyl-1,6,8- trioxadispiro[4.1..]pentadecane (18) 2 2 Bn Me Me TBDPS R f (hexanes/etac 4:1) = 0.19; [ ] D 20.8 (c 0.27 in CCl ); IR ν max (film)/cm , 292, 284, 172, 161, 114, 1428, 162, 101, 1249, 1194, 1071, 100, 822, 78, 701, 619; 1 NMR (00 Mz, CDCl ): (4, m), (1, m), 6.87 (2, d, J = 8.8 z), 4.4 (1, d, J = 12.1 z), 4.49 (1, d, J = 11.4 z), 4.7 (1, d, J = 11.4 z), 4.4 (1, d, J = 12.1 z), (1, m), (, m),.79 (, s), (, m),. (, s), (2, m), (7, m), (2, m), (12, m); 1 C NMR (7 Mz, CDCl ): C 19.1, 18.2, 1.7, 1.6, 1.9, 10.7, 129., 129.4, 128., 127.6, 127., 114.8, 11.8, 96.7, 8., 78.8, 77.8, 7.6, 72.8, 71.1, 70.2, 67.1, 66.8,., 41.1, 41.0, 9.4, 4.1, 1.7, 29.1, 26.8, 19., 12.; RMS Found (ESI): (M + Na) +, 8.408, C Na 9 Si requires 8.40.
6 (2S,S,R,7S,9S,11S,1S,1S)--(Benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1 -(4- methoxybenzyloxy)ethan-2 -yl)-11-methoxy-1-methyl-1,6,8-trioxadispiro[4.1..]pentadecan- 1-yl imidazole-1-carbothioate S 2 2 Bn Me Im Me TBDPS R f (hexanes/etac 2:1) = 0.19; [ ] D (c 0.10 in CCl ); IR ν max (film)/cm , 2929, 287, 1710, 161, 114, 146, 186, 1284, 1247, 1096, 1027, 969, 824, 741, 702; 1 NMR (00 Mz, CDCl ): 8.4 (1, br s), (, m), (11, m), 7.20 (2, d, J = 8.8 z), 7.04 (1, br s), 6.82 (2, d, J = 8.8 z), (1, m), 4. (1, d, J = 12.1 z), (, m), (1, m),.96 (1, dd, J = 11.6,. z),.79 (1, dd, J = 11.6, 4.7 z),.77 (, s),.74.6 (1, m),.6.49 (2, m),.22 (, s), 2.99 (1, dd, J = 17.6, 4.8 z), 2.7 (1, dd, J = 17.6, 7. z), (2, m), (, m), (1, m), (2, m), (1, m), (12, m); 1 C NMR (7 Mz, CDCl ): C 211.9, 19.0, 17.8, 16.9, 1., 12.9, 129.8, 129.1, 128., 128.1, 127.8, 127.7, 127., 127., 11.4, 11.7, 82., 81.7, 78.8, 78.1, 7.2, 72., 71.1, 67., 64.4, 7.2,., 41., 40.9, 9.9, 6.1,., 29.7, 26.7, 19.2, 12.1; RMS Found (ESI): M +, , C 2 6 N 2 9 SSi requires (2S,S,R,7S,9S,11S,1S)--(Benzyloxy)-9-((tert-butyldiphenylsilyloxy)methyl)-2-(1 -(4- methoxybenzyloxy)ethan-2 -yl)-11-methoxy-1-methyl-1,6,8-trioxadispiro[4.1..]pentadecane () 2 2 Bn Me Me TBDPS 1 NMR (400 Mz, CDCl ): (4, m), (1, m), 6.8 (2, d, J = 8.6 z), 4.2 (1, d, J = 12.1 z), 4.41 (1, d, J = 11.4 z), (2, m), (2, m), (1, m),.77 (, s),.7.70 (1, m),.6.62 (2, m),.8.47 (2, m).26 (, s), 2.8 (1, dd, J = 17.0, 7.1 z), 2.6 (1, dd, J = 17.0,. z), (, m), (, m), (1, m), (12, m); RMS Found (ESI): M +, , C Na 8 Si requires
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