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Total Synthesis of Gramistilbenoids A, B, and C
Journal of Natural Products ( IF 5.1 ) Pub Date : 2018-04-03 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00865
Dipesh S. Harmalkar 1 , Qili Lu 1 , Kyeong Lee 1
Affiliation  

Stilbenes are biologically active metabolites of plants that have the potential to attenuate a broad range of human diseases. Gramistilbenoids are a class of natural products with a stilbene skeleton, isolated from the bamboo orchid (Arundina graminifolia), and with significant cytotoxicity against cancer cell lines (NB4, A549, SHSY5Y, PC3, and MCF7). These are the first identified naturally occurring diphenylethylenes to possess a hydroxyethyl unit. However, some of these compounds are not abundant in nature, and thus, their synthesis is advantageous. This paper reports the first synthesis of gramistilbenoids A (1), B (2), and C (3), with overall yields of 10, 2, and 8% respectively. These natural products were synthesized using key reactions, such as Horner–Wadsworth–Emmons olefination, Stille coupling, and hydroboration–oxidation.

中文翻译:

Gramistilbenoids A,B和C的全合成

对苯二酚是植物的生物活性代谢产物,具有减轻广泛人类疾病的潜力。禾本科类固醇是一类具有二苯乙烯骨架的天然产物,从竹兰花(Arundina graminifolia)中分离出来,并且对癌细胞系(NB4,A549,SHSY5Y,PC3和MCF7)具有明显的细胞毒性。这些是首先鉴定的具有羟乙基单元的天然存在的二苯基乙烯。然而,这些化合物中的一些在性质上并不丰富,因此它们的合成是有利的。本文报告了香豆素类化合物A(1),B(2)和C(3)的首次合成),总产量分别为10%,2%和8%。这些天然产物是通过关键的反应合成的,例如霍纳-沃兹沃思-埃蒙斯烯化,斯蒂尔偶联和硼氢化-氧化。
更新日期:2018-04-03
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