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Stille and Suzuki Cross‐Coupling Reactions as Versatile Tools for Modifications at C‐17 of Steroidal Skeletons – A Comprehensive Study
Author(s) -
Koch Vanessa,
Nieger Martin,
Bräse Stefan
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601289
Subject(s) - stille reaction , chemistry , tributyltin , steroid , coupling reaction , combinatorial chemistry , suzuki reaction , halide , natural product , organic chemistry , stereochemistry , palladium , biochemistry , catalysis , hormone
Abstract Herein, we report on a comparative Stille and Suzuki cross‐coupling study of steroidal vinyl (pseudo)halides with different boronic acids and tributyltin organyls. Furthermore, we have investigated the “inverse” case of those cross‐coupling reactions, i.e., the reaction of a steroidal vinylpinacolatoborane or a tributyltin steroid with various bromides. The development of both methods allows the introduction of different residues at C‐17 of steroid skeletons providing access to a broad variety of steroid analogues which are of high interest for biological screenings or natural product synthesis.