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

  • 1 Begley MJ, Campbell RV, Crombie L, Whiting DA. J. Chem. Soc. 1971; 3634
    • 2a Jahng Y, Park JG. Molecules 2018; 23: 3107
    • 2b Alberti Á, Riethmüller E, Béni S. J. Pharm. Biomed. Anal. 2018; 147: 13
    • 2c Zhu J, Islas-Gonzalez G, Bois-Choussy M. Org. Prep. Proced. Int. 2000; 32: 505
    • 2d Sun C, Huang H, Xu C, Li X, Chen K. Plant Foods Hum. Nutr. 2013; 68: 97
    • 3a Gulder T, Baran PS. Nat. Prod. Rep. 2012; 29: 899
    • 3b Joshi BS, Pelletier SW, Newton MG, Lee D, McGaughey GB, Puar MS. J. Nat. Prod. 1996; 59: 759
    • 4a Tao J, Morikawa T, Toguchida I, Ando S, Matsuda H, Yoshikawa M. Bioorg. Med. Chem. 2002; 10: 4005
    • 4b Wang M, Liu Y, Pan RL, Wang RY, Ding SL, Dong WR, Sun GB, Ye JX, Sun XB. Int. J. Mol. Med. 2019; 43: 2133
    • 4c Kubo M, Yamazaki M, Matsuda H, Matsuo K, Asanuma Y. Biol. Pharm. Bull. 2002; 24: 259
    • 5a Shen S, Liao Q, Feng Y, Liu J, Pan R, Lee SM. Y, Lin L. Food Chem. 2019; 270: 305
    • 5b Shen S, Liao Q, Liu J, Pan R, Lee SM. Y, Lin L. J. Cachexia Sarcopenia Muscle 2019; 10: 429
    • 5c Cao Y, Chen X, Deng S, Li Z, Xu T, Yu G, Yu Y, Yuan G, Zhang M. CN 108434127A, 2018
    • 5d Shen S, Liao Q, Pan R, Lin L. Br. J. Pharmacol 2019; 176: 3983
  • 6 Dai GH, Meng GM, Tong YL, Chen X, Ren ZM, Wang K, Yang F. Phytomedicine 2014; 21: 1490
  • 7 Martin MD, Calcul L, Smith C, Jinwal UK, Fontaine SN, Darling A, Seeley K, Wojtas L, Narayan M, Gestwicki JE, Smith GR, Reitz AB, Baker BJ, Dickey CA. ACS Chem. Biol. 2015; 10: 1099
  • 8 Mohamed SE. N, Whiting DA. J. Chem. Soc., Perkin Trans. 1 1983; 2577
  • 9 Bochicchio A, Schiavo L, Chiummiento L, Lupattelli P, Funicello M, Hanquet G, Choppin S, Colobert F. Org. Biomol. Chem. 2018; 16: 8859
    • 10a Meidlinger D, Marx L, Bordeianu C, Choppin S, Colobert F, Speicher A. Angew. Chem., Int. Ed. 2018; 57: 9160
    • 10b Norouzi-Arasi H, Salom-Roig XJ, Lanners S, Hanquet G. Curr. Org. Synth. 2017; 15: 105
    • 10c Bensoussan C, Rival N, Hanquet G, Colobert F, Reymond S, Cossy J. Nat. Prod. Rep. 2014; 31: 468
    • 10d Chiummiento L, Funicello M, Lopardo MT, Lupattelli P, Choppin S, Colobert F. Eur. J. Org. Chem. 2012; 188
    • 10e Ferreiro-Mederos L, Lanners S, Henchiri H, Fekih A, Hanquet G. Nat. Prod. Res. 2009; 23: 256
    • 10f Bonini C, Chiummiento L, Pullez M, Solladié G, Colobert F. J. Org. Chem. 2004; 69: 5015
    • 11a Dansou B, Pichon C, Dhal R, Brown E, Mille S. Eur. J. Org. Chem. 2000; 1527
    • 11b Harrowven DC, Woodcock T, Howes PD. Tetrahedron Lett. 2002; 43: 9327
    • 12a Lecourt C, Dhambri S, Allievi L, Sanogo Y, Zeghbib N, Ben Othman R, Lannou M.-I, Sorin AJ. Nat. Prod. Rep. 2018; 35: 105 ; and references cited therein
    • 12b Cheng-Sanchez I, Sarabia F. Synthesis 2018; 50: 3749
  • 13 Chausset-Boissarie L, Arvai R, Cumming GR, Besnard CE, Kündig EP. Chem. Commun. 2010; 46: 6264
    • 14a Clavier H, Caijo F, Borré E, Rix D, Boeda F, Nolan SP, Mauduit M. Eur. J. Org. Chem. 2009; 4254
    • 14b Tracz A, Matczak M, Urbaniak K, Skowerski K. Beilstein J. Org. Chem. 2015; 11: 1823
    • 14c Boeda F, Clavier H, Nolan SP. Chem. Commun. 2008; 2726
  • 15 Christiansen E, Due-Hansen ME, Urban C, Merten N, Pfleiderer M, Karlsen KK, Rasmussen SS, Steensgaard M, Hamacher A, Schmidt J, Drewke C, Petersen RK, Kristiansen K, Ullrich S, Kostenis E, Kassack MU, Ulven T. ACS Med. Chem. Lett. 2010; 1: 345
  • 16 Gomtsyan A. Org. Lett. 2000; 2: 11
  • 17 Lalic G, Corey EJ. Org. Lett. 2007; 9: 4921
  • 18 Yuen AK. L, Hutton CA. Tetrahedron Lett. 2005; 46: 7899
  • 19 Molander GA, Biolatto B. J. Org. Chem. 2003; 68: 4302
  • 20 Chatterjee AK, Choi TL, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360
  • 21 Bäckvall J.-E, Andreasson U. Tetrahedron Lett. 1993; 34: 5459
  • 22 Jun YueC, Liu Y, He R. J. Mol. Catal. A: Chem. 2006; 259: 17
  • 23 Whiting DA, Wood AF. Tetrahedron Lett. 1978; 19: 2335
  • 24 Preparation of 20 A solution of 18 (1 equiv, 51 mg, 0.091 mmol) in toluene (180 mL) was degassed for 30 min under a flow of argon. The reaction mixture was heated at reflux. Then, GII (20 mol%, 15 mg, 0.018 mmol) was added in one portion. The reaction mixture was stirred at reflux for 16 h. The reaction mixture was filtered through a pad of both activated charcoal and silica gel, and the solvent was evaporated under reduced pressure to afford 20 (20 mg, 35 mmol, 39%) as an oil. 1H NMR (500 MHz, CDCl3): δ = 7.50–7.44 (m, 4 H), 7.43–7.34 (m, 6 H), 7.27–7.20 (m, 10 H), 7.14–7.00 (m, 2 H), 6.98 (d, J = 2.3 Hz, 2 H), 6.87 (d, J = 8.4 Hz, 2 H), 6.70–6.65 (m, 4 H), 5.97 (d, J = 16.0 Hz, 2 H), 5.13–5.08 (m, 4 H), 5.05–4.90 (m, 4 H), 3.99–3.82 (m, 6 H), 3.64 (s, 6 H), 2.94–2.71 (m, 8 H), 2.57–2.48 (m, 4 H), 2.46–2.35 (m, 4 H). 13C NMR (125 MHz, CDCl3): δ = 203.21, 154.64, 150.68, 150.13, 146.32, 138.01, 137.64, 133.60, 131.36, 131.31, 128.82, 128.72, 128.65, 128.36, 128.16, 128.13, 127.62, 127.08, 126.66, 113.24, 75.29, 70.76, 61.00, 60.97, 41.91, 33.25, 29.84, 29.02. HRMS (ESI+): m/z calcd for C70H68NaO10 [M + Na]+: 1091.4705; found: 1091.4700.
  • 25 Hoye TR, Jeffrey CS, Tennakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
    • 26a Wallace DJ. Angew. Chem. Int. Ed. 2005; 44: 1912
    • 26b Wang X, Bowman EJ, Bowman BJ, Porco JA. Angew. Chem. Int. Ed. 2004; 43: 3601
  • 27 Lipshutz BH, Petersen TB, Abela AR. Org. Lett. 2008; 10: 1333
  • 28 Hong SH, Sanders DP, Lee CW, Grubbs RH. J. Am. Chem. Soc. 2005; 127: 17160