103233-25-6Relevant academic research and scientific papers
Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol
Nguyen, Minh H.,Imanishi, Masashi,Kurogi, Taichi,Smith, Amos B.
, p. 3675 - 3678 (2016)
Anion relay chemistry (ARC), an effective, multicomponent union tactic, was successfully employed for the total synthesis of the highly cytotoxic marine macrolide (-)-mandelalide A (1). The northern hemisphere was constructed via a new type II ARC/CuCN cross-coupling tactic, while the southern hemisphere was secured via a highly efficient four-component type I ARC union. Importantly, the synthesis of 1 showcases ARC as a rapid, scalable coupling strategy for the union of simple readily available building blocks to access diverse complex molecular fragments with excellent stereochemical control.
Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy
Nguyen, Minh H.,Imanishi, Masashi,Kurogi, Taichi,Wan, Xuemei,Ishmael, Jane E.,McPhail, Kerry L.,Smith, Amos B.
, p. 4287 - 4306 (2018)
The mandelalides comprise a family of structurally complex marine macrolides that display significant cytotoxicity against several human cancer cell lines. Presented here is a full account on the development of an Anion Relay Chemistry (ARC) strategy for the total synthesis of (-)-mandelalides A and L, the two most potent members of the mandelalide family. The design and implementation of a three-component type II ARC/cross-coupling protocol and a four-component type I ARC union permits rapid access respectively to the key tetrahydrofuran and tetrahydropyran structural motifs of these natural products. Other highlights of the synthesis include an osmium-catalyzed oxidative cyclization of an allylic 1,3-diol, a mild Yamaguchi esterification to unite the northern and southern hemispheres, and a late-stage Heck macrocyclization. Synthetic mandelalides A and L displayed potent cytotoxicity against human HeLa cervical cancer cells (EC50, 1.3 and 3.1 nM, respectively). This synthetic approach also provides access to several highly potent non-natural mandelalide analogs, including a biotin-tagged mandelalide probe for future biological investigation.
A Tactically Novel Alternative to Acyclic Stereoselection Based on the Concept of a Replicating Chiron - 1,3- and 1,4-C-Methyl Substitution
Hanessian, Stephen,Murray, Peter J.,Sahoo, Soumya P.
, p. 5627 - 5630 (2007/10/02)
A chiral 4-hydroxymethyl butenolide is used as a template for the stereocontrolled conjugate addition of a C-methyl group.A sequential two-carbon extension and reformation of a lactone with the new side-chain leads to a "replicated" butenolide, which is s
