Synthesis of (+)-Lavandulol by the Prins Reaction

Abstract

Ueno et al.¹ have just described the synthesis of (+)-lavandulol² (3) in 57% yield by reaction of the stannane (1) with trioxanecatalysed by BF₃. Without detracting from the elegance of this route we wish to point out that the analogous transformation can be carried out more directly and cheaply by subjecting the hydrocarbon (2) to the Lewis acid-catalysed Prins reaction.³ Furthermore, the hydrocarbon (2) reacts satisfactorily with paraformaldehyde, which is ineffective¹ for the stannane (1).