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<A NAME="RG23307ST-9">9</A>
Typical Procedure and Selected Data for Compound 9: In a 10-mL round-bottomed flask under argon, 7 (100 mg, 0.16 mmol) and 4-chlorobenzaldehyde (22 µL, 1.2 equiv) were dissolved in
freshly distilled THF (1 mL) at -78 °C, then a 1 M solution of LiHMDS in THF (383
µL, 2.4 equiv) was added dropwise over 5 min. Stirring was maintained during 30 min
at -78 °C and then at r.t. for 1 h. After hydrolysis, the mixture was extracted with
EtOAc (3 × 10 mL), dried over Na2SO4, concentrated by rotary evaporation and purified by flash chromatography to afford
the desired product (63 mg, 0.115 mmol); yield: 72%; yellow liquid; [α]D
22 -1 (c = 1, acetone); R
f
0.44 (EtOAc-PE, 1:9). 1H NMR (300 MHz, CD3COCD3): δ = 3.89-3.96 (m, 3 H, 2 × H-8, H-6), 4.21-4.26 (m, 1 H, H-7), 4.31 (dd, J = 3.3, 5.7 Hz, 1 H, H-5), 4.61-4.88 (m, 6 H, OCH
2Ph), 5.25 (d, J = 3.3 Hz, 1 H, H-4), 6.67 (d, J = 15.9 Hz, 1 H, HC=C), 6.94 (d, J = 15.9 Hz, 1 H, HC=C), 7.27-7.40 (m, 17 H, ArH), 7.50 (d, J = 8.7 Hz, 2 H, ArH). 13C NMR (75 MHz, CD3COCD3): δ = 69.4 (CH2), 70.9 (CH2), 73.7 (CH2), 73.8 (CH2), 75.3 (CH), 76.9 (CH), 77.9 (CH), 103.4 (CH), 124.9 (CH), 128.2 (C), 128.2 (CH),
128.3 (CH), 128.3 (CH), 128.5 (CH), 128.6 (CH), 128.6 (CH), 129.0 (CH), 129.1 (CH),
129.6 (CH), 133.7 (C), 136.5 (C), 139.6 (C), 139.8 (C), 151.9 (C), 163.2 (C). MS (ESI+):
m/z (%) = 575.2 [M + Na]+. HRMS (ESI): m/z [M + Na]+ calcd for C35H33ClO4Na: 575.1965; found: 575.1969.