Racemic tetrahydropyran 3 was efficiently synthesised from allylsilane 6 and aldehyde 7 via an intramolecular Sakurai cyclisation. In a single step, the relative configuration of three chiral centres was established. Allylsilane 6 was readily assembled from 1-iodo-1-selenopropene 10, a synthetic equivalent of a propene 1,1-dianion. (c) 2005 Elsevier Ltd. All rights reserved.
Perez-Balado, C., & Marko, I. (2005). A connective approach to the tetrahydropyran subunit of polycavernoside A via a novel 1,1-dianion equivalent. Tetrahedron Letters, 46(29), 4887-4890. https://doi.org/10.1016/j.tetlet.2005.05.054 (Original work published 2005)