Aldol condensation reactions of tricarbonyliron complexes. Towards building blocks for the synthesis of carbomycin B/tylosin macrolide antibiotics and fluorinated analogs

Tricarbonyliron complexes of α-methoxyheptadienone 3 and octadienone 8 were reacted as silyl enol ethers with protected β-hydroxypropanal and TiCl 4, to give the syn– syn aldol condensation products 4 and 11 as major, isolated diastereomers (61 and 45%). Products 4 and 11 were converted into key int...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2000-05, Vol.41 (21), p.4219-4222
Main Authors: Franck-Neumann, Michel, Geoffroy, Philippe, Gumery, Fabien
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Tricarbonyliron complexes of α-methoxyheptadienone 3 and octadienone 8 were reacted as silyl enol ethers with protected β-hydroxypropanal and TiCl 4, to give the syn– syn aldol condensation products 4 and 11 as major, isolated diastereomers (61 and 45%). Products 4 and 11 were converted into key intermediates of previous total syntheses of carbonolide B and tylonide, in a few steps, including the iron-directed reduction to syn diols and partial ozonolysis. The same methodology was used for the high yielding synthesis of a monofluorinated analog.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00569-4