Synlett 2020; 31(06): 559-564
DOI: 10.1055/s-0039-1691523
cluster
© Georg Thieme Verlag Stuttgart · New York

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

Paul Massé
a  Laboratoire 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
a  Laboratoire 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
b  Department of Science, University of Basilicata, Via dell’Ateneo lucano, 10, 85100 Potenza, Italy   Email: lucia.chiummiento@unibas.it
,
Gilles Hanquet
a  Laboratoire 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
a  Laboratoire 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
› Author Affiliations
We thank the Centre National de la Recherche Scientifique (CNRS), France as well as the University of Strasbourg, and Paul Massé is grateful to the French Ministry of Research and Development for financial support.
Further Information

Publication History

Received: 14 October 2019

Accepted after revision: 17 November 2019

Publication Date:
29 November 2019 (online)


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.

Supporting Information

 
  • References and Notes

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