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. 2014 Apr 10;5(6):679–684. doi: 10.1021/ml500077j

Scheme 4. Improved Synthesis of 4.

Scheme 4

Reagents and conditions: (a) nBuLi, BnOH, −10 °C to RT, THF; (b) NBS, DCM, −10 °C to RT; (c)(i) nBuLi, −100 °C, 2-Me-THF, (ii) 34 containing C7 isomer, −100 °C to RT; (d) BF3·OEt2, Et3SiH, DCM, −78 °C, 15 min; (e) acetamide, Pd2(dba)2, xantphos, Cs2CO3, 130 °C, 1 h; (f) H2, MeOH, Pd–C (10%), RT to 50 °C, 70 h; (g) NaOMe, RT to 80 °C.