Medium-Sized Cyclic Ethers via Stevens [1,2]-Shift of Mixed Monothioacetal-Derived Sulfonium Ylides: Application to Formal Synthesis of (+)-Laurencin

Rongrong Lin, Liya Cao, F. G. West

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

A novel approach to medium-sized cyclic ethers was devised using a Stevens [1,2]-shift of a sulfonium ylide derived from a readily accessible six-membered mixed-monothioacetal precursor. The concise and efficient transformation offers a surprising degree of chirality transfer with observed retention of stereochemical configuration on the anomeric migrating carbon and has been applied as the key step in an enantioselective formal synthesis of (+)-laurencin.

Original languageEnglish (US)
Pages (from-to)552-555
Number of pages4
JournalOrganic Letters
Volume19
Issue number3
DOIs
StatePublished - Feb 3 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

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