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

Paul Massé (1) , Sabine Choppin (1) , Lucia Chiummiento (2) , Gilles Hanquet (1) , Francoise Colobert (1)

1 LIMA - Laboratoire d'innovation moléculaire et applications
2 UNIBAS - Università degli studi della Basilicata [Potenza]

A convergent approach for the synthesis of (±)-myricanol, a strained diarylheptanoid isolated from Myricacae, was undertaken using a Suzuki-Miyaura coupling followed by a 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 RRCM conditions.

Mots clés: myricanol; target-oriented synthesis; diarylheptanoid; natural product; macrocycle; Suzuki-Miyaura cross-coupling; RCM; Alzheimer's disease biological activities

Domaines: Chimie

Paul Massé, Sabine Choppin, Lucia Chiummiento, Gilles Hanquet, Francoise Colobert. Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-metacyclophane. SYNLETT, 2019, 31 (06), pp.559-564. ⟨10.1055/s-0039-1691523⟩. ⟨hal-03075499⟩