Controlled Synthesis of Enantio-, Regio-, and Diastereomers of Amino-4-pentenediols from 1,4-Pentadien-3-ol via Epoxy-4-pentenols I.erythro-1-Amino-4-pentene-2,3-diols

All articles of this category erythro -1-Amino-4-pentene-2,3-diols 7 , 8 of both the L- and D-series are readily accessible in high purity from 1,4-pentadien-3-ol via the 1,2-epoxy-4-pentenols 2 , 4 by treatment with ammonia, primary aliphatic or aromatic amines, secondary aliphatic or a heterocyclic amine (imidazole, 6j ). 9-(2,3-Dihydroxy-4-penten-1-yl)adenines of the erythro -L- and -D-form 7k , 8k are obtained from 2 (L- erythro ) via 1-chloro-4-pentene-2,3-diol ( 9 ) and from D-ribonolactone via the 1-mesyloxy-4-pentene-2,3-diol ( 12 ) (D- erythro ), respectively.