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Organocatalytic Asymmetric Formation of Steroids
Author(s) -
Halskov Kim Søholm,
Donslund Bjarke S.,
Barfüsser Sebastian,
Jørgensen Karl Anker
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400203
Subject(s) - substituent , stereoselectivity , chemistry , organocatalysis , ring (chemistry) , heteroatom , optically active , sulfone , combinatorial chemistry , catalysis , enantioselective synthesis , estrone , stereochemistry , organic chemistry , biochemistry , hormone
A novel and simple one‐step approach for the construction of optically active steroids in a highly stereoselective manner by using organocatalysis is presented. The reaction of (di)enals with cyclic dienophiles in the presence of a TMS‐protected prolinol catalyst leads to the construction of important 14 β‐steroids. This new reaction allows an easy access to optically active steroids with a variety of substituents in the A ring in high yields and up to greater than 99 % ee . The reaction has been extended to include the construction of B ‐ and D ‐homosteroids as well as steroids containing heteroatoms in the B ring. The angular substituent at C13 can be varied and alkyl, ester, and sulfone functionalities are introduced with excellent stereoselectivities. Simple synthetic procedures provide access to a range of naturally occurring steroids such as estrone and related analogues.