Synthetic Studies of Carolacton: Enantioselective Total Synthesis of C1–C8 and C9–C19 Fragments of the Molecule

Kulakarni Sripad Rao; Subhash Ghosh

doi:10.1055/s-0033-1339500

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(19): 2745-2751
DOI: 10.1055/s-0033-1339500

paper

Synthetic Studies of Carolacton: Enantioselective Total Synthesis of C1–C8 and C9–C19 Fragments of the Molecule

Kulakarni Sripad Rao

Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India Fax: +91(40)27193108 eMail: sripadchem@gmail.com

,

Subhash Ghosh*

Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India Fax: +91(40)27193108 eMail: sripadchem@gmail.com

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Abstract

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Abstract

This paper describes synthetic studies towards carolacton, a highly potent antibiotic against dental caries and endocarditis related bacterium Streptococcus mutans. The synthesis of the 12-membered lactone with a diversely functionalized keto acid side chain was accomplished by utilizing a blend of chiral pool and aldol strategies. Carbon chain C1–C8 was derived by utilizing Paterson aldol methodology and a Corey–Fuchs reaction. The C9–C19 chain was prepared by means of iterative Evans asymmetric alkylations and an E-selective cross-metathesis reaction.

Key words

Streptococcus mutans - carolacton - antibiotic - Paterson aldol reaction - cross metathesis

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References and Notes

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