Green Process of Three-Component Prostaglandin Synthesis and Rapid 11 C Labelings for Short-Lived PET Tracers: Highly Polished C-Couplings Revolutionizing Advances in Bio- and Medical Sciences
Green Process of Three-Component Prostaglandin Synthesis and Rapid 11 C Labelings for Short-Lived PET Tracers: Highly Polished C-Couplings Revolutionizing Advances in Bio- and Medical Sciences
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三组分前列腺素合成的绿色工艺和短寿命 PET 示踪剂的快速 11 C 标记：高度抛光的 C 偶联彻底改变了生物和医学科学的进步
DOI：
10.5772/intechopen.72868
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发表时间：
2018
影响因子：
2.8
通讯作者：
H. Doi
中科院分区：
文献类型：
--
作者：
Masaaki Suzuki;H. Koyama;H. Ishii;Koichi Kato;M. Ögren;H. Doi
基于一锅法三组分偶联，使用有机铜或有机锌酸酯缀合物加成到4-羟基-2-环戊烯酮，然后用有机卤化物捕获所得烯醇化物的组合，已经完成了洋地黄素（PGs）的一般合成。基于这种合成方法的使用，还合成了生物学上重要的PG衍生物，包括ent-Δ-PGA 1、15 SAPNIC（[ H]APNIC）和15 R-TIC。最终，有机锌酸酯共轭加成与通过有机三氟甲磺酸酯的烯醇化物捕集相结合，导致实际的绿色三组分偶联，其包括使用化学计量量的三种组分（烯酮、α和ω-侧链，比例接近1：1：1），而不使用HMPA和重金属。已经建立了将短寿命的C和F放射性核素引入碳框架的一般方法，通过使用Pd介导的[C]甲基碘和有机三丁基锡烷或有机硼酸盐之间的快速交叉偶联来开发快速C-[C]甲基化和C-[F]氟甲基化;或[F]氟甲基溴和有机硼酸盐，允许合成多种生物学上重要的和疾病导向的PET探针，例如15 R-[C]TIC。此外，Pd介导的快速C-[C]羰基化使用[C]CO和有机硼酸酯在环境温度和常压下使用常规的氦载气已被探索。此外，在大气压下使用[C]CO2和有机硼酸盐与Rh催化剂促进了C-[C]羧化。
General synthesis of prostaglandins (PGs) has been accomplished based on a one-pot three-component coupling using a combination of organocopper or organozincate conjugate addition to 4-hydroxy-2-cyclopentenone followed by trapping of resulting enolate with an organic halide. Based on the use of this synthetic methodology, biologically significant PG derivatives including ent-Δ-PGA1, 15SAPNIC ([ H]APNIC), and 15R–TIC have also been synthesized. Ultimately, organozincate conjugate addition combined with the enolate trapping by an organic triflate results in practical green threecomponent coupling comprising the use of stoichiometric amounts of three components (enone, αand ω-side chains in a nearly 1:1:1 ratio) without using HMPA and heavy metals. General methodology for introducing short-lived C and F radionuclides into carbon frameworks has been established by developing rapid C-[C]methylation and C-[F]fluoromethylation using Pd-mediated rapid cross-coupling between [C]methyl iodide and an organotributylstannane or organoboronate; or [F]fluoromethyl bromide and organoboronate, respectively, allowing the synthesis of a wide variety of biologically significant and disease-oriented PET probes such as 15R-[C]TIC. Moreover, Pdmediated rapid C-[C]carbonylation using [C]CO and organoboronate at ambient temperature under atmospheric pressure using conventional helium carrier gas has been explored. Further, C-[C]carboxylation has been promoted using [C]CO2 and organoboronate with Rh catalyst under atmospheric pressure.
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影响因子：
16.6
作者：
Riss, Patrick J.;Lu, Shuiyu;Telu, Sanjay;Aigbirhio, Franklin I.;Pike, Victor W.
通讯作者：
Pike, Victor W.
影响因子：
15
作者：
Netherton, MR;Dai, CY;Fu, GC
通讯作者：
Fu, GC
新型碳11标记吡啶醚的合成和生物学评价：用于大脑中α4β2烟碱乙酰胆碱受体（α4β2-nAChRs）正电子发射断层扫描体内成像的候选配体。
影响因子：
3.5
作者：
Gao,Yongjun;Ravert,HaydenT;Kuwabara,Hiroto;Xiao,Yingxian;Endres,ChristopherJ;Hilton,John;Holt,DanielP;Kumar,Anil;Alexander,Mohab;Wong,DeanF;Dannals,RobertF;Horti,AndrewG
通讯作者：
Horti,AndrewG
影响因子：
15
作者：
Littke, AF;Schwarz, L;Fu, GC
通讯作者：
Fu, GC