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Ring‐Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E 2 ‐1,15‐Lactone
Author(s) -
Fürstner Alois,
Grela Karol
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000403)39:7<1234::aid-anie1234>3.0.co;2-v
Subject(s) - ring closing metathesis , stereoselectivity , metathesis , chemistry , total synthesis , lactone , ring (chemistry) , natural product , stereochemistry , alkyne , olefin metathesis , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
The first total synthesis of a biologically relevant natural product (prostaglandin E 2 ‐1,5‐lactone; see picture) by ring‐closing diyne metathesis followed by Lindlar reduction is reported. This conceptually novel strategy allows the stereoselective formation of macrocyclic Z alkenes which cannot be accessed stereoselectively by conventional ring‐closing olefin metathesis.