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1 article(s) from Reguera, Leslie

Steroid diversification by multicomponent reactions

Leslie Reguera,
Cecilia I. Attorresi,
Javier A. Ramírez and
Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

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Graphical Abstract

Figure 1: Structures of natural steroids of A) animal and B) plant origin.

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Scheme 1: Synthesis of a steroidal β-lactam by Ugi reaction of a cholanic aldehyde [14].

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Scheme 2: Synthetic route to steroidal 2,5-diketopiperazines based on a diastereoselective Ugi-4CR with an an...

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Scheme 3: Multicomponent synthesis of a heterocycle–steroid hybrid using a ketosteroid as carbonyl component [18]....

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Scheme 4: Synthesis of peptidomimetic–steroid hybrids using the Ugi-4CR with spirostanic amines and carboxyli...

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Scheme 5: Synthesis of azasteroids using the Ugi-4CR with androstanic and pregnanic carboxylic acids [22].

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Figure 2: Ugi-4CR-derived library of androstanic azasteroids with diverse substitution patterns at the phenyl...

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Scheme 6: Synthesis of 4-azacholestanes by an intramolecular Ugi-4C-3R [26].

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Scheme 7: Synthesis of amino acid–steroid hybrid by multiple Ugi-4CR using steroidal isocyanides [29].

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Scheme 8: Synthesis of ecdysteroid derivatives by Ugi-4CR using a steroidal isocyanide [30].

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Scheme 9: Stereoselective multicomponent synthesis of a steroid–tetrahydropyridine hybrid using a chiral bifu...

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Scheme 10: Pd(II)-catalyzed three-component reaction with an alkynyl seco-cholestane [34].

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Scheme 11: Multicomponent synthesis of steroid–thiazole hybrids from a steroidal ketone [36].

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Scheme 12: Synthesis of cholanic pseudo-peptide derivatives by novel MCRs based on the reactivity of ynamide [37,38].

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Scheme 13: Synthesis of steroid-fused pyrimidines and pyrimidones using the Biginelli-3CR [39,42,43].

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Scheme 14: Synthesis of steroidal pyridopyrimidines by a reaction sequence comprising a 4CR followed by a post...

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Scheme 15: Synthesis of steroid-fused pyrimidines by MCR of 2-hydroxymethylene-3-ketosteroids [46].

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Scheme 16: Synthesis of steroid-fused naphthoquinolines by the Kozlov–Wang MCR using ketosteroids [50,51].

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Scheme 17: Conjugation of steroids to carbohydrates and peptides by the Ugi-4CR [62,63].

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Scheme 18: Solid-phase multicomponent conjugation of peptides to steroids by the Ugi-4CR [64].

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Scheme 19: Solid-phase multicomponent conjugation of peptides to steroids by the Petasis-3CR [68].

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Scheme 20: Synthesis of steroidal macrobicycles (cages) by multiple multicomponent macrocyclizations based on ...

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Scheme 21: One-pot synthesis of steroidal cages by double Ugi-4CR-based macrocyclizations [76].

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Review

Published 06 Jun 2019

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