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Issue 31, 2019
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Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

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Abstract

The convergent total synthesis of naturally occurring paecilomycin C is described here for the first time. Asymmetric Brown allylation, E-selective cross metathesis, and a biomimetic carboxylate assisted intramolecular nucleophilic ring opening of an epoxide were employed to access the enantiopure γ-lactone framework of the natural product. Late stage E-selective Julia–Kocienski olefination was then employed to furnish the natural product in an efficient way.

Graphical abstract: Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

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Publication details

The article was received on 06 Jul 2019, accepted on 16 Jul 2019 and first published on 17 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01504C
Org. Biomol. Chem., 2019,17, 7369-7379

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    Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

    J. Chakraborty and S. Nanda, Org. Biomol. Chem., 2019, 17, 7369
    DOI: 10.1039/C9OB01504C

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