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Stereoselective Synthesis of Steroids and Related Compounds, V. Synthesis of (±)‐Chokol A by a Tandem Michael‐Addition/Dieckmann Cyclization
Author(s) -
Groth Ulrich,
Halfbrodt Wolfgang,
Köhler Thomas,
Kreye Paul
Publication year - 1994
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.199419940907
Subject(s) - chemistry , tandem , stereoselectivity , conjugate , bromide , yield (engineering) , michael reaction , total synthesis , stereochemistry , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy , composite material
A total synthesis of (±)‐chokol A ( rac ‐ 12 ) was accomplished in five steps by starting from the α,β‐unsaturated ester ( E )‐ 2 in an overall yield of 24%. The key step of this synthesis is the tandem conjugate addition/Dieckmann cyclization of the cuprate derived from vinyl bromide 9 with the α,β‐unsaturated ester ( E )‐ 2 .