An Iterative and Convergent Synthesis of Syn Polyols

Article abstract of DOI:10.1021/jo00031a041

We have developed a new iterative and convergent synthesis of alternating (1,3,5...) polyol chains based on enantiomerically enriched (94percent ee) chloro nitrile 1.Chloro nitrile 1 is both a potential nucleophile and a potential electrophile; orthogonal nucleophilic or electrophilic activation leads to a highly efficient synthetic strategy for alternating polyol chains.As an illustration permethylated polyol 2 (n= 10), a natural product with 10 stereogenic centers isolated from the blue green alga Tolypothrix conglutinata var. chlorata, was prepared in 10 steps from 1.