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. 2016 Oct 24;7:13196. doi: 10.1038/ncomms13196

Figure 2. A–B and B–C paring pathways for synthesis of scaffolds I–III.

Figure 2

Reagents and conditions: (i) NaBH4, MeOH, 0 °C→r.t. then Boc2O, TEA, DCM, 0 °C→r.t.; (ii) EtI, NaH, DMF, 0 °C→r.t.; (iii) Pd(OH)2/C, H2, MeOH, then MsCl, TEA, DCM, 0 °C→r.t.; (iv) BnBr, ACN, 80 °C, then RMgBr, THF, −78 °C→r.t.; (v) Grubbs' second-generation catalyst (20 mol%), toluene, reflux; and (vi) NaBH4, MeOH, 0 °C→r.t., then allyl bromide, TEA, DMF, 0 °C→r.t. TIPS, triisopropylsilyl; TEA, triethylamine; MsCl, methanesulfonyl chloride; BnBr, benzyl bromide; ACN, acetonitrile. [a]Determined by LC-MS analysis of crude reaction mixture and by 1H NMR analysis of samples purified by short silica-gel column. [b]Yield of the isolated major diastereomer. [c]Determined by LC-MS analysis of crude reaction mixture. 1H NMR, proton nuclear magnetic resonance. LC-MS, liquid chromatography-mass spectrometry.