Protected γ-Ketoaldehyde Synthesis. 1-Ipomeanol

Abstract

γ-Ketoaldehydes¹ are often employed as intermediates in cyclopentenone synthesis. In our rethrolone synthesis, we employed the reaction of a 2-alkylated-2-lithio-1,3-dithiane (I, R=n-pentyl, n=1).² We wish to report an extension of that approach to the synthesis of a γ-protected-γ-ketoaldehyde (III, R=Me, n=2), which we have utilized in a new synthesis of 1-Ipomeanol (6), a toxic substance found in mold-damaged sweet potatoes.³