Steric effects on deprotonative generation of cyclohexynes and 1,2-cyclohexadienes from cyclohexenyl triflates by magnesium amides

A concise, racemic total synthesis of three sesquiterpenoid alkaloids (greenwaylactams A-C) exhibiting an unprecedented 8-membered benzolactam is disclosed. Key transformations of this work include the ring expansion through cleavage of an indole via Witkop oxidation, as well as an HFIP mediated cationic cyclisation to build up the pentacyclic carbon skeleton. 

pdf/a-biomimetic-approach-for-the-concise-total-synthesis-of-37a6pjcbu5.pdf

A biomimetic approach for the concise total synthesis of greenwaylactams A–C

Cyclooctyne molecules have found wide applications in the strain-promoted azide–alkyne cycloaddition (SPAAC) reactions, which avoid the biotoxicity caused by the use of Cu(I) catalysts. Among the various cyclooctyne systems, dibenzocyclooctyne (DBCO) series have displayed the highest reaction activity. However, the synthesis processes of such structures are time-consuming, which to some extent limit their large-scale development and application. This review has summarized current synthesis routes of two DBCO molecules, aza-dibenzocyclooctyne (DIBAC) and biarylazacyclooctynone (BARAC).

/pdf/a-short-review-of-research-progress-on-the-synthesis-2iaqunmt.pdf

A Short Review of Research Progress on the Synthesis Approaches of Aza-Dibenzocyclooctyne Derivatives

This chapter discusses the creative synthetic approaches to azides and cycloalkynes, provides the rationale for controlling SPAAC reactivity through tuning cycloalkyne and azide backbone modifications, and highlights research on nitrone cycloadditions with cycloalkynes. This synthetic and knowledge toolset will help in the design of better cycloalkynes and their partners to answer challenging research questions and aid the development of new applications.

4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity

p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles.

Deprotonative formation of biarylazacyclooctynone (BARAC) from the corresponding enol triflate is described. The reaction furnished the azacyclooctynone within one hour at –78 °C. This process could be performed in one pot from the starting ketone to provide a range of BARAC derivatives in moderate to excellent yields. The protocol enabled the gram-scale formation of the BARAC skeleton by reducing the number of reaction steps. Furthermore, the established method was applied to the synthesis of the BARAC derivative bearing a coumarin moiety.

/pdf/one-pot-deprotonative-synthesis-of-biarylazacyclooctynones-3bn1st2nlr.pdf

One-Pot Deprotonative Synthesis of Biarylazacyclooctynones

Individual evaluation of aging- and caloric restriction-related changes to distinct multimeric complexes of circulating adiponectin by immunoblotting

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One-Pot Deprotonative Synthesis of Biarylazacyclooctynones

Individual evaluation of aging- and caloric restriction-related changes to distinct multimeric complexes of circulating adiponectin by immunoblotting