Cyclic Alkenenitriles: Synthesis, Conjugate Addition, and Stereoselective Annulation
作者:Fraser F. Fleming、Zhiyu Zhang、Qunzhao Wang、Omar W. Steward
DOI:10.1021/jo0345291
日期:2003.10.1
methylthiomethyl-protected hydroxyalkenenitriles that are easily hydrolyzed for subsequent annulations with omega-chloroalkyl Grignard reagents. Deprotonating the gamma-hydroxyalkenenitriles with t-BuMgCl followed by addition of omega-chloroalkyl Grignard reagents triggers a conjugate addition-alkylation sequence leading exclusively to cis-octalins, hydrindanes, and decalins. Stereoelectronic control favors an axial
Cyclizations and fragmentations in the alkylation of 6‐chloro‐5‐hydroxy‐4‐aminopyrimidines with aminoalkyl chlorides
作者:Edwige M. H. Picazo、Amy B. Heptinstall、David M. Wilson、Céline Cano、Bernard T. Golding、Michael J. Waring
DOI:10.1002/jhet.4228
日期:2021.4
Substituted aminopyrimidines are an important class of compounds, in part because they frequently show biological activity. Facilesynthesis of polysubstituted aminopyrimidines is highly desirable for the synthesis of screening libraries. We describe a route to 4,6‐diamino‐5‐alkoxypyrimidines via a SNAr‐alkylation‐SNAr sequence from readily available 4,6‐dichloro‐5‐methoxypyrimidine, which allows the
取代的氨基嘧啶是一类重要的化合物,部分原因是它们经常表现出生物活性。多取代氨基嘧啶的简便合成对于筛选文库的合成是非常理想的。我们描述了一种通过 S N Ar-烷基化-S N Ar 序列从容易获得的 4,6-二氯-5-甲氧基嘧啶合成 4,6-二氨基-5-烷氧基嘧啶的路线,这使得可以通过区域化学控制合成此类化合物。将这种方法扩展到带有氨基取代基的烷化剂,会产生意想不到的、在某些情况下是前所未有的产物,这些产物是由分子内 S N Ar 环化和随后的断裂产生的。
Synthesis of new Benzo[f]isoindole-4,9-diones as anticancer compounds
AbstractThe design and synthesis of monosubstituted and disubstituted azanaphthoquinone annelated pyrroles with anticancer activity are described. N-alkylation with various side chains at the pyrrole ring led to a series of monosubstituted products. For preparation of disubstituted isoindole derivatives, appropriately substituted tosyl methyl isocyanides were used. The biological activity of all the
Synthesis of HC-Toxin via Matteson Homologation and C–H Functionalization
作者:Michael Kohr、Uli Kazmaier
DOI:10.1021/acs.joc.3c00914
日期:2023.8.4
host-specific HC-toxin was developed. The HC-toxin belongs to a group of cyclic, tetrapeptide histone deacetylase inhibitors containing the unusual amino acid Aeo. Key steps in the synthesis of this building block include the Matteson homologation to generate the stereogenic centers in the side chain and a C–H functionalization to connect the side chain to a protected alanine.
开发了一种针对宿主特异性 HC 毒素的新合成路线。HC-毒素属于一组环状四肽组蛋白脱乙酰酶抑制剂,含有不常见的氨基酸 Aeo。合成该结构单元的关键步骤包括用于在侧链中生成立体中心的 Matteson 同系化以及用于将侧链连接到受保护的丙氨酸的 C-H 功能化。
Cross‐Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion
atom. CCR of axially chiral alkenyl sulfoximines with Ni(PPh3)2Cl2 as a precatalyst and ZnPh2 does not require salt promotion and is stereoretentive. The reaction with Zn(CH2SiMe3)2, however, demands salt promotion and is not stereoretentive. CCR of axially chiralα‐methylated alkenyl sulfoximines afforded persubstituted axially chiralalkenes with high selectivity. Alkenyl (N‐triflyl)sulfoximines