Convergent synthesis of a polyol chain with 4-acetoxy-1,3-dioxanes using a 1,1-bis((trimethylsilyl)methyl)ethene linchpin

Article abstract of DOI:10.1016/S0040-4039(98)80014-2

The symmetric dinucleophile, 1,1-bis((trimethylsilyl)methyl)ethene, was used as a linchpin to join two different 4-acetoxy-1,3-dioxanes. These couplings produce anti-diols, and were used to prepare a segment of the roflamycoin polyol. The anti-diol selectivity normally observed on coupling 4-acetoxy-1,3-dioxanes was found to be a function of the C2 acetal substituent, and tert-butyl was superior to methyl.