TY - JOUR AU - Massé, Paul; Choppin, Sabine; Chiummiento, Lucia; Hanquet, Gilles; Colobert, Françoise TI - Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-Metacyclophane SN - 0936-5214 SN - 1437-2096 PY - 2020 JO - Synlett JF - Synlett LA - EN VL - 31 IS - 06 SP - 559 EP - 564 ET - 2019/11/29 DA - 2020/03/16 KW - myricanol KW - target-oriented synthesis KW - diarylheptanoid KW - natural product KW - macrocycle KW - Suzuki–Miyaura cross-coupling KW - RCM KW - ­Alzheimer’s disease KW - biological activities AB - 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. PB - © Georg Thieme Verlag DO - 10.1055/s-0039-1691523 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0039-1691523 ER -