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Synthesis 2020; 52(12): 1795-1803
DOI: 10.1055/s-0039-1690852
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

Gianluca Casotti 
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
,
Graziano Fusini
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
,
Matteo Ferreri
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
,
Luca Fidia Pardini
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
,
Claudio Evangelisti∗
b   CNR, Istituto di Chimica dei Composti Organometallici (ICCOM), Via G. Moruzzi 1, 56124, Pisa, Italy   Email: claudio.evangelisti@cnr.it
,
Gaetano Angelici  ∗
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
,
Adriano Carpita
a   Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: gaetano.angelici@unipi.it
› Author AffiliationsFinancial support from the University of Pisa (PRA 2018_23) is gratefully acknowledged.
Further Information

Publication History

Received: 16 January 2020

Accepted after revision: 18 February 2020

Publication Date:
05 March 2020 (online)

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In loving memory of Prof. Adriano Carpita

Abstract

Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira­ cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization of the Sonogashira­ couplings allowed the use of catalysts supported on different matrices with good results in terms of catalytic efficiency and yields.

Key words

Asparenydiol - Sonogashira cross-coupling - Mitsunobu etherification - total synthesis - solid-supported palladium catalyst

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690852.
  • Supporting Information
 

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