1,4- and 1,5-Stereoselection by Sequential Aldol Addition to α,β-Unsaturated Aldehydes Followed by Claisen Rearrangement. Application to Total Synthesis of the Vitamin E Side Chain and the Archaebacterial C40 Diol

Article abstract of DOI:10.1021/jo00244a017

A synthetic strategy has been developed wherein the high 1,2-stereoselection obtainable from aldol reaction of an α,β-unsaturated aldehyde is parlayed by a subsequent Claisen rearrangement into 1,4- or 1,5-stereoselection.For example, diol monoethers 26 a