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

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

• References and Notes

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