Ac acetate; Bz benzoate; PG protecting group; Tris 2,4,6-triisopropylphenylsulfonyl; TES triethylsilyl; TBAF tetrabutylammonium fluoride.
[9] A detailed analysis of the synthesis of the metathesis precursors will be reported elsewhere.
[10] S. D. Edwards, T. Lewis, R. J. K. Taylor, Tetrahedron Lett. 1999, 40, 4267 ± 4270. [11] Schrocks molybdenum catalyst was not used with 12, as it is known to be incompatible with free OH groups.
[12] The stereochemistry of 13 was determined by correlation with (Z)-18, whose synthesis will be reported elsewhere.
[13] X-ray structure data: Nonius KappaCCD diffractometer, f and w scans, Mo Ka radiation (l 0.71073 ), graphite monochromator, T 150 K, structure solution with maXus, [14] refinement against F 2 (SHELXL-97 [15] ) with anisotropic thermal parameters for all nonhydrogen atoms, hydrogen positions were calculated with riding isotropic thermal parameters. Data collection for 14: crystal dimensions 0.20 Â 0.20 Â 0.20 mm 3 , monoclinic, space group P2 1 /c, a 8.7890(3), b 20.7820(3), c 9.9300(8) , a 90.0000(19), b 107.7280(16), g 90.0000(19)8, V 1727.61(15) 3 , Z 4, 1 calcd 1.124 g cm À3 , m 0.070cm À1 , F(000) 648, q max 27.488, h, k, l ranges: 0 11, 0 26, À12 12, 3958 data collected, 3958 unique data (R int 0.025), 3378 data with I b 2s(I), 196 parameters refined, GOF(F 2 ) 1.058, final R indices (R 1 S k F o j À j F c k /S j F o j, wR 2 [Sw 2 o ÀF 2 c 2 / Sw(F 2
o 2 ] 1/2 ): R 1 0.0425, wR 2 0.1083, max./min. residual electron density 0.266(0.038)/ À 0.180(0.038) e A À 3 . Data collection for 18: crystal dimensions 0.20 Â 0.20 Â 0.20 mm 3 , monoclinic, space group P2 1 /c, a 8.4850(4), b 15.6940(5), c 13.9450(7) , a 90.000(3), b 106.2550(18), g 90.000(3)8, V 1782.73(14) 3 , Z 4, 1 calcd 1.186 g cm À 3 , m 0.078cm À 1 , F(000) 696, q max 30.038, À 11 h 9, À 22 k 14, À 12 l 19, 10 513 data collected, 5193 unique data (R int 0.036), 4160 data with I b 2s(I), 212 parameters refined, GOF(F2) 1.038, final R ind : R 1 0.0475, wR 2 0.1320, max./min. residual electron density 0.431(0.046)/ À 0.396(0.046) e A À 3 . Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-135213 and 135214. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK