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Enantioselective Synthesis of Paraconic Acids
Author(s) -
Chhor Rakeshwar B.,
Nosse Bernd,
Sörgel Sebastian,
Böhm Claudius,
Seitz Michael,
Reiser Oliver
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390019
Subject(s) - enantioselective synthesis , lewis acids and bases , total synthesis , chemistry , metathesis , catalysis , formal synthesis , combinatorial chemistry , stereochemistry , organic chemistry , polymer , polymerization
The development of a new method for the enantioselective synthesis of disubstituted γ ‐butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (−)‐roccellaric acid, (−)‐nephrosteranic acid and (−)‐protopraesorediosic acid, and the formal total synthesis of (−)‐methylenolactocin and (−)‐protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper( I )‐catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium( II )‐catalyzed, intermolecular cross metathesis reactions.