Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from Rhodomyrtus tomentosa and Their Asymmetric Biomimetic Synthesis.

作者: Yao-Lan Li , Chuang-Chuang Li , Wei Tang , Wen-Cai Ye , Ren-Wang Jiang

DOI: 10.1021/ACS.ORGLETT.1C01616

关键词:

摘要: Rhodomentosones A and B (1 and 2), two pairs of novel enantiomeric phloroglucinol trimers featuring a unique 6/5/5/6/5/5/6-fused ring system were isolated from Rhodomyrtus tomentosa. Their structures with absolute configurations were elucidated by NMR spectroscopy, X-ray crystallography, and ECD calculation. The bioinspired syntheses of 1 and 2 were achieved in six steps featuring an organocatalytic asymmetric dehydroxylation/Michael addition/Kornblum–DeLaMare rearrangement/ketalization cascade reaction …

参考文章(48)
Maël Charpentier, Marcus Hans, Johann Jauch, Enantioselective Synthesis of Myrtucommulone A European Journal of Organic Chemistry. ,vol. 2013, pp. 4078- 4084 ,(2013) , 10.1002/EJOC.201300179
Marius Morkunas, Martin E. Maier, Alternative routes to the acylphloroglucinol rhodomyrtone Tetrahedron. ,vol. 71, pp. 9662- 9666 ,(2015) , 10.1016/J.TET.2015.10.063
Giovanni Appendino, Federica Bianchi, Alberto Minassi, Olov Sterner, Mauro Ballero, Simon Gibbons, Oligomeric acylphloroglucinols from myrtle (Myrtus communis) Journal of Natural Products. ,vol. 65, pp. 334- 338 ,(2002) , 10.1021/NP010441B
Takahiko Akiyama, Stronger Brønsted acids Chemical Reviews. ,vol. 107, pp. 5744- 5758 ,(2007) , 10.1021/CR068374J
Anthony R. Carroll, Jasmine Lamb, Roger Moni, Gordon P. Guymer, Paul I. Forster, Ronald J. Quinn, Myrtucommulones F-I, phloroglucinols with thyrotropin-releasing hormone receptor-2 binding affinity from the seeds of Corymbia scabrida. Journal of Natural Products. ,vol. 71, pp. 1564- 1568 ,(2008) , 10.1021/NP800247U
Asadhawut Hiranrat, Wilawan Mahabusarakam, New acylphloroglucinols from the leaves of Rhodomyrtus tomentosa Tetrahedron. ,vol. 64, pp. 11193- 11197 ,(2008) , 10.1016/J.TET.2008.09.054
Inder Pal Singh, Jasmeen Sidana, Sandip B. Bharate, William J. Foley, Phloroglucinol compounds of natural origin: Synthetic aspects Natural Product Reports. ,vol. 27, pp. 393- 416 ,(2010) , 10.1039/B914364P
M Iqbal Choudhary, Noureen Khan, Manzoor Ahmad, Sammer Yousuf, Hoong-Kun Fun, Samreen Soomro, M Asif, M Ahmed Mesaik, Farzana Shaheen, None, New inhibitors of ROS generation and T-cell proliferation from Myrtus communis. Organic Letters. ,vol. 15, pp. 1862- 1865 ,(2013) , 10.1021/OL4002976
John W. van Klink, Joseph J. Brophy, Nigel B. Perry, Rex T. Weavers, β-Triketones from Myrtaceae: Isoleptospermone from Leptospermum scoparium and Papuanone from Corymbia dallachiana Journal of Natural Products. ,vol. 62, pp. 487- 489 ,(1999) , 10.1021/NP980350N