ChemInform Abstract: Stereoselective Construction of Acyclic Structures with Four Consecutive Asymmetric Centers.
Abstract
The synthesis of all the eight possible diastereomers of 6,8-dihydroxy-5,7-dimethyltridecane is described as shown for (VIII) and (XI).
ChemInform Abstract
The synthesis of all the eight possible diastereomers of 6,8-dihydroxy-5,7-dimethyltridecane is described as shown for (VIII) and (XI). The key steps are a newly introduced stereoselective epoxidation of β-methylhomoallylic alcohols and the subsequent alkylative opening of the epoxide rings. Thus, anti-epoxidation of the nonprotected homoallylic alcohol (V) gives the epoxide (VI), which undergoes ring-opening and methylation to give the title compound (VIII). In contrast, syn-epoxidation is achieved using the silyl-protected homoallylic alcohol (IX), which is converted into the title compound (XI). In conclusion, the choice of the protecting group as well the epoxidation agent allows the stereoselective construction of four consecutive asymmetric centers.
