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Total Synthesis of Leukotrienes from Butadiene
Author(s) -
Rodríguez Ana,
Nomen Miguel,
Spur Bernd W.,
Godfroid JeanJacques,
Lee Tak H.
Publication year - 2000
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 - 10.1002/1099-0690(200009)2000:17<2991::aid-ejoc2991>3.0.co;2-h
Subject(s) - chemistry , epimer , sharpless epoxidation , stereochemistry , catalysis , asymmetric induction , total synthesis , organic chemistry , enantioselective synthesis
The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium‐catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee . Simple transformations of the key intermediate 15 produced the leukotrienes LTA 4 methyl ester ( 4 ), LTC 4 ( 1 ), LTD 4 ( 2 ) and LTE 4 ( 3 ), as well as (14 S ,15 S )‐LTA 4 methyl ester ( 24 ) and the novel [ 2 H 2 ]‐LTA 4 methyl ester ( 28 ). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB 4 .