Abstract

The first asymmetric total synthesis of both enantiomers of the natural products colletorin A and colletochlorin A is presented. The proposed methodology is based on the coupling reaction between highly substituted aromatic Gilman cuprates and optically active allyl bromides, in turn obtained by Sharpless asymmetric dihydroxylation. The latter ensured a high degree of regio- and stereocontrol in the enantioselective step of the synthesis. The same synthetic strategy has been also applied for the preparation of differently halogenated synthetic analogues of colletochlorin A in high enantiomeric purity. The enantioselective synthesis of colletorin A and colletochlorin A allows to reliably assign their absolute configuration. Preliminary assessment of their herbicidal and insecticidal properties evidence the possibility to modulate the bioactivity of these compounds, highlighting its dependence on both the absolute stereochemistry and the halogen nature. (C) 2018 Elsevier Ltd. All rights reserved.

Autore Pugliese

• Casella Francesca , Zonno Maria

Tutti gli autori

• Marsico G.; Pignataro B.A.; Masi M.; Evidente A.; Casella F.; Zonno M.C.; Tak J.-H.; Bloomquist J.R.; Superchi S.; Scafato P.

Titolo volume/Rivista

Tetrahedron

Anno di pubblicazione

2018

ISSN

0040-4020

ISBN

Non Disponibile

Numero di citazioni Wos

Nessuna citazione

Ultimo Aggiornamento Citazioni

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Numero di citazioni Scopus

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Ultimo Aggiornamento Citazioni

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Settori ERC

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Codici ASJC

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