Transition-Metal-Mediated or -Catalyzed Syntheses of Steroids and Steroid-Like Compounds

This short review aims to summarize recent advances in the use of transition‐metal‐catalyzed and ‐mediated methodology for the synthesis of steroid and steroid‐like skeletons reported in the last decade. The methodologies used include transition‐metal‐catalyzed or ‐mediated [2+2+2] and other cycload...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2012-01, Vol.2012 (1), p.29-42
Main Authors: Kotora, Martin, Hessler, Filip, Eignerová, Barbara
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Asymmetric synthesis
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Steroids
Synthesis design
Synthetic methods
Transition metals
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Summary:This short review aims to summarize recent advances in the use of transition‐metal‐catalyzed and ‐mediated methodology for the synthesis of steroid and steroid‐like skeletons reported in the last decade. The methodologies used include transition‐metal‐catalyzed or ‐mediated [2+2+2] and other cycloadditions, the Pauson–Khand reaction, cross‐coupling and Heck reactions, processes based on the activation of single and multiple bonds, metathesis reactions, hydrovinylation, and other reactions. Several examples of total synthesesof steroid compounds [e.g., (+)‐ and (–)‐estrone, desogestrel] by these procedures are presented. Recent advances in the synthesis of compounds containing steroid skeletons are summarized. Emphasis is on the application of transition‐metal‐mediated and‐catalyzed methodologies based on Zr, Fe, Ru, Co, Rh, Ni, Pd, Pt, Au, and Sm compounds. In addition, several examples of total syntheses of steroid compounds or their biologically relevant derivatives are given.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201100921