Transition-Metal-Catalyzed Reactions in Steroid Synthesis (original) (raw)

Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods

European Journal of Organic Chemistry, 2020

The rich biology associated with steroids dictates a growing demand for the new synthetic strategies that would improve the access to natural and unnatural representatives of this family. The recent advances in the field of catalysis have 2. Syntheses Enabled by Transition Metal Catalysis 2.1. Enantioselective Palladium-Catalyzed Dearomatizative Cyclization for the Synthesis Steroid Boldenone Core [8] Chiral phenanthrenone derived tricyclic cores bearing allcarbon quaternary centers are present in numerous complex [a] Dr.

Application of olefin metathesis in the synthesis of steroids

Steroids, 2011

Over the past decade, ruthenium-mediated metathesis transformations, including cross-metathesis, ring-closing metathesis, enyne metathesis, ring-opening metathesis polymerization, and also tandem processes, belong to the most intensively studied reactions. Many applications of olefin metathesis in the synthesis of natural products have been recently described. Also in the field of steroid chemistry new methods of total synthesis and hemisynthesis based on metathesis reactions have been elaborated. Various biologically active compounds, e.g. vitamin D and hormone analogues, steroid dimers and macrocycles, etc. have been prepared using a variety of olefin-metathesis protocols.

Steroid diversification by multicomponent reactions

Beilstein Journal of Organic Chemistry, 2019

Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

Recent Highlights in Green Oxidative Chemical Processes Applied to Steroid Chemistry

InTech eBooks, 2016

Steroids and their oxidation products are widely distributed in living organisms and are important intermediates for the synthesis of many biologically active molecules. Due to their pharmacological and synthetic relevance, several oxidative chemical processes for the functionalization of the steroid nucleus have been developed. Green chemistry principles have been incorporated in some oxidative transformations of steroids, allowing significant advances in synthetic chemistry applied to these compounds. This chapter presents a selection of relevant applications of pharmaceutical green chemistry to steroid's oxidative processes. Special emphasis is given to catalytic processes encompassing heterogeneous nanocatalysts, whose application in this context is increasing over the past years. This chapter is organized according to the reaction type that includes alcohol oxidation, epoxidation of alkenes, and allylic oxidation of alkenes to enones, among other relevant oxidative transformations. Biocatalytic oxidative methods applied to steroid synthesis are not included in this review.