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. 2022 Mar 3;27(5):1677. doi: 10.3390/molecules27051677

Scheme 26.

Scheme 26

Synthesis of precursor 202, as reported by Ogawa and Kobayashi [105]. Reagents and conditions: i. CH2=CHOEt PPTS; ii. BuLi then EtBr, DMPU; iii. 3 N HCl, 71% over the three steps; iv. tBuOOH D-DIPT, Ti(OPr)4, –20 °C, 12 h, 48% for 206, 99% ee and 46% for 207, 99% ee; v. Br2; vi. TBAF, vii. TBSCl, 65% over the three steps; viii. PrNH2, CuI, Pd (PPh3)4, 89%; ix. H2, Pd/BaSO4, EtOAc, 94%; x. K2CO3, MeOH, 90%; xi. Sia2BH (1.5 equiv.), 0 °C, 1 h, THF.