Premium
Short, Highly Enantioselective Synthesis of a Key Intermediate for the Preparation of Leucotriene B 4 and Its 14,15‐Didehydro Derivative
Author(s) -
Nunn Kurt,
Mosset Paul,
Grée René,
Saalfrank Rolf W.
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198811881
Subject(s) - enantioselective synthesis , yield (engineering) , chemistry , derivative (finance) , combinatorial chemistry , alcohol , triple bond , stereochemistry , medicinal chemistry , double bond , organic chemistry , catalysis , materials science , business , metallurgy , finance
The butadiene(tricarbonyl)iron complex (−)‐1 can be converted almost diastereospecifically ( de ≥ 98%) into the (CO 3 )Fe‐protected homopropargyl alcohol 3 by reaction with allenylsilane 2 (yield 65%). The triple bond in 3 can be stereospecifically reduced to a cis double bond. Decomplexation of the product or direct complexation of 3 affords key intermediates for the synthesis of leucotriene B 4 and 14,15‐didehydroleucotriene B 4 , respectively.