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Cyclobutanone Approach to the Synthesis of Cardenolides
Author(s) -
Błaszczyk Krzysztof,
Koenig Hanna,
Paryzek Zdzisław
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400580
Subject(s) - chemistry , butenolide , cyclobutanone , androstane , total synthesis , cycloaddition , stereochemistry , yield (engineering) , cardenolide , diene , organic chemistry , glycoside , ring (chemistry) , materials science , natural rubber , metallurgy , catalysis
17β‐(3‐Oxocyclobutyl)androstane, prepared by the thermal [2 + 2] cycloaddition of dichloroketene to 3β‐acetoxypregna‐5,20‐diene, is the key intermediate in the new, efficient synthesis of steroids bearing the 17β‐butenolide fragment that characterizes cardenolides. The six‐step synthesis of 3β‐ tert ‐butyldimethylsilyloxy‐14α‐carda‐5,20(22)‐dienolide was achieved with a total yield of 32%. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)