Asymmetric Synthesis of the Fully Functional Macrolide Core of 
Salicylihalamide:  Remote Control of Olefin Geometry during RCM

Fürstner, Alois; Thiel, Oliver R.; Blanda, Gaetano

doi:10.1021/ol006646d

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Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide: Remote Control of Olefin Geometry during RCM

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel, Oliver R.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Blanda, Gaetano
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Thiel, O. R., & Blanda, G. (2000). Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide: Remote Control of Olefin Geometry during RCM. Organic Letters, 2(23), 3731-3734. doi:10.1021/ol006646d.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-34D9-D

Abstract

A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of β-keto esters 13 and 16 catalyzed by [(R)-BINAP·RuCl₂]₂·NEt₃ and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the latter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.