Issue 17, 2016

Total synthesis of laidlomycin

Abstract

The synthesis of laidlomycin is described. With an established stereocontrolled synthetic route to the aldehyde 5, the known β-keto phosphonate 4 was coupled with 5 and the resulting enone was subjected to a sequential hydrogenolysis/hydrogenation and equilibration process to effect the correct spiroketalization for the natural product. The stereogenic carbons were elaborated by desymmetrization for C12, allylation for C13, vanadyl-induced epoxidation for C16, Zn(BH4)2 reduction for C17, a chiral building block for C18 and C24, Shi epoxidation for C20 and C21, Myers’ alkylation for C22, and thermodynamic control for C25.

Graphical abstract: Total synthesis of laidlomycin

Supplementary files

Article information

Article type
Communication
Submitted
31 Dec 2015
Accepted
28 Jan 2016
First published
04 Feb 2016

Chem. Commun., 2016,52, 3536-3539

Total synthesis of laidlomycin

W. Lee, S. Kang, B. Jung, H. Lee and S. H. Kang, Chem. Commun., 2016, 52, 3536 DOI: 10.1039/C5CC10673G

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