Simple 1,3-dienes undergo highly stereoselective hetero-Diels-Alder additions with SO2 at low temperature giving sultines. These reactions that are faster than the more exothermic cheletropic additions of SO2-producing sulfolenes. This has led to the invention of a new C-C bond-forming reaction combining electron-rich dienes and alkenes with SO2. The reaction cascade has been exploited to develop combinatorial, one-pot, four-component syntheses of polyfunctional sulfones, sulfonamides, and sulfonic esters. It also allows us to generate, in one-pot operations, enantiomerically enriched polypropionate fragments containing up to three contiguous stereogenic centers and a (E)-alkene unit. These fragments can be used directly in further C-C bond-forming reactions, such as cross-aldol condensations, thus permitting the expeditious construction of complicated natural products of biological interest (e.g., Baconipyrones, Rifamycin S, Apoptolidinone) and analogues. New ene reactions of SO2 have also been discovered; they open new avenues to organic synthesis.
This work presents the first electrochemical preparation of alkyl arylsulfonates by direct anodic oxidation of electron‐rich arenes. The reaction mechanism features a multi‐component reaction consisting of electron‐rich arenes, an alcohol of choice and excess SO
2
in an acetonitrile‐HFIP reaction mixture. In‐situ formed monoalkyl sulfites are considered as key intermediates with bifunctional purpose. Firstly, this species functions as nucleophile and secondly, excellent conductivity is provided. Several primary and secondary alcohols and electron‐rich arenes are implemented in this reaction to form the alkyl arylsulfonates in yields up to 73 % with exquisite selectivity. Boron‐doped diamond electrodes (BDD) are employed in divided cells, separated by a simple commercially available glass frit.
This review covers recent literature from 2012-2019 concerning 170 marine natural products
and their semisynthetic analogues with strong anticancer biological activities. Reports that shed light on
cellular and molecular mechanisms and biological functions of these compounds, thus advancing the
understanding in cancer biology are also included. Biosynthetic studies and total syntheses, which have
provided access to derivatives and have contributed to the proper structure or stereochemistry elucidation
or revision are mentioned. The natural compounds isolated from marine organisms are divided into
nine groups, namely: alkaloids, sterols and steroids, glycosides, terpenes and terpenoids, macrolides,
polypeptides, quinones, phenols and polyphenols, and miscellaneous products. An emphasis is placed
on several drugs originating from marine natural products that have already been marketed or are currently
in clinical trials.
Clinical trials have evidenced that several natural compounds, belonging to the phytochemical classes of alkaloids, terpenes, phenols and flavonoids, are effective for the management of various types of cancer. Latest research has proven that natural products and their semisynthetic variants may serve as a starting point for new drug candidates with a diversity of biological and pharmacological activities, designed to improve bioavailability, overcome cellular resistance, and enhance therapeutic efficacy. This review was designed to bring an update regarding the anticancer potential of betulonic acid and its semisynthetic derivatives. Chemical derivative structures of betulonic acid including amide, thiol, and piperidine groups, exert an amplification of the in vitro anticancer potential of betulonic acid. With the need for more mechanistic and in vivo data, some derivatives of betulonic acids may represent promising anticancer agents.
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