Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones.

08:00 EDT 1st April 2019 | BioPortfolio

Summary of "Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones."

A chiral Brønsted acid catalyzed highly enantio- and diastereoselective cascade cyclization has been developed to streamline the synthesis of valuable multifunctionalized enantioenriched cyclopenta[ f]pyrrolo[1,2- d][1,4]diazepinones bearing three contiguous stereocenters in high yields with excellent control of stereochemistry from a wide range of both readily available 2-furylcarbinols and (1 H-pyrrol-1-yl)anilines, which represents the first asymmetric intramolecular conjugate addition of α,β-unsaturated cycloketones with inert N-substituted pyrroles as well as the first enantioselective aza-piancatelli rearrangement/Friedel-Crafts alkylation cascade reaction.


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Name: Organic letters
ISSN: 1523-7052


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RNA that has catalytic activity. The catalytic RNA sequence folds to form a complex surface that can function as an enzyme in reactions with itself and other molecules. It may function even in the absence of protein. There are numerous examples of RNA species that are acted upon by catalytic RNA, however the scope of this enzyme class is not limited to a particular type of substrate.

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An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.

Compounds with three contiguous nitrogen atoms in linear format, H2N-N=NH, and hydrocarbyl derivatives.

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