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. Author manuscript; available in PMC: 2010 Jan 25.
Published in final edited form as: Science. 2007 Aug 31;317(5842):1189–1192. doi: 10.1126/science.1146421

Fig. 2.

Fig. 2

(A) Structural and stereochemical patterns explained by the Nakanishi hypothesis of ladder polyether biosynthesis. (B) The two transition states (fused and spiro) and products (THP (6) and THF (7), respectively) for cyclization of an exemplary epoxy alcohol via epoxide opening. (C) Templated epoxide-opening cyclizations. (D) Dependence of THP:THF (6:7) selectivity on pH in cyclization of 5. (E) Enhancement of conversion of 5 and of THP:THF selectivity by H2O. Me, methyl; THF, tetrahydrofuran; THP, tetrahydropyran.