Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-Metacyclophane

Paul Massé; Sabine Choppin; Lucia Chiummiento; Gilles Hanquet; Françoise Colobert

doi:10.1055/s-0039-1691523

Synlett, Table of Contents

Synlett 2020; 31(06): 559-564
DOI: 10.1055/s-0039-1691523

cluster

Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-Metacyclophane

Paul Massé

^aLaboratoire d’Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de Haute- Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, France Email: sabine.choppin@unistra.fr

,

Sabine Choppin∗

^aLaboratoire d’Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de Haute- Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, France Email: sabine.choppin@unistra.fr

,

Lucia Chiummiento∗

^bDepartment of Science, University of Basilicata, Via dell’Ateneo lucano, 10, 85100 Potenza, Italy Email: lucia.chiummiento@unibas.it

,

Gilles Hanquet

^aLaboratoire d’Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de Haute- Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, France Email: sabine.choppin@unistra.fr

,

Françoise Colobert

^aLaboratoire d’Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de Haute- Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, France Email: sabine.choppin@unistra.fr

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Abstract

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Published as part of the ISySyCat2019 Special Issue

Abstract

A convergent approach for the synthesis of (±)-myricanol, a strained diarylheptanoid isolated from Myricacae, was undertaken using a Suzuki–Miyaura coupling followed by a ring-closing metathesis (RCM). Herein, we report the unintentional formation of a 26-membered macrocycle as RCM product resulting from a head-to-tail dimerization of the seco-precursor, even in relay ring-closing metathesis (RRCM) conditions.

Key words

myricanol - target-oriented synthesis - diarylheptanoid - natural product - macrocycle - Suzuki–Miyaura cross-coupling - RCM - Alzheimer’s disease - biological activities

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References

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