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. Author manuscript; available in PMC: 2010 Sep 9.

Published in final edited form as: J Am Chem Soc. 2009 Sep 9;131(35):12524–12525. doi: 10.1021/ja904179f

Scheme 1 — Synthetic route to C13-modified saxitoxins.^a

^a(a) Cl₃CCH₂C(O)Cl, C₅H₅N, 0 °C, 93%; (b) ⁱPr₂NEt, CH₃CN, 86%; (c) 10 mol% OsCl₃, Oxone, 44%; (d) RNH₂, THF, 77–99%; (e) B(O₂CCF₃)₃, 92%; (f) DCC, DMSO, C₅H₅NH^{+ −}O₂CCF₃, 63%. Mbs = p-methoxybenzenesulfonyl.