Nicolaou, K. C.;Yu, Ruocheng;Lu, Zhaoyong;Alvarez, Fernando G. published 《Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations》. The research results were published in《Journal of the American Chemical Society》 in 2022.Product Details of 39637-74-6 The article conveys some information:
The synthesis of functionalized aromatic compounds is a central theme of research for modern organic chem. Despite the increasing finesse in the functionalization of five- and six-membered aromatic rings, their seven-membered-ring sibling, tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), remains a challenging target for synthetic derivatization. This challenge primarily emanates from the unique structural and chem. properties of tropolonoid compounds, which often lead to unexpected and undesired reaction outcomes under conditions developed for the functionalizations of other aromatic moieties. Herein, the authors describe the total synthesis of one of the most complex natural tropolonoids, gukulenin B (I). The synthetic route features a series of site-selective aromatic C-H bond functionalizations and C-C bond formations, whose reaction conditions are judiciously tuned to allow uncompromised performance on the tropolone nucleus. The flexibility and modularity of the synthesis are expected to facilitate further synthetic and biol. studies of the gukulenin family of cytotoxins. In addition, the methods and tactics developed herein for the functionalization of the tropolone moiety could inspire and enable chemists of multiple disciplines to take advantage of this privileged yet underexplored structural motif.(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6) were involved in the experimental procedure.
(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6 Product Details of 39637-74-6) is a chiral derivatizing agent. It can be prepared by reacting (-)-(1S,4R)-camphanic acid with thionyl chloride.
Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics