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Total Synthesis of 6‐Methyl‐5‐androstene‐3,11,17‐trione 3‐Ethylene Acetal, Building Block for 6α‐Methylprednisolone
Author(s) -
Daniewski Andrzej Robert,
Piotrowska Emilia
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1989198901100
Subject(s) - chemistry , acetal , ethylene , catalysis , potassium , salt (chemistry) , sulfone , organic chemistry , medicinal chemistry , block (permutation group theory) , total synthesis , geometry , mathematics
The total synthesis of 6‐methyl‐5‐androstene‐3,11,17‐trione 3‐ethylene acetal ( 25 ) in 13 steps is described. The coupling reaction of the potassium salt of tert ‐butyl α‐propionylpropionate with the readily available sulfone 2 , followed by catalytic hydrogenation and acidic cyclization, are the key steps of this synthesis.