Enantioselective Synthesis of Paraconic Acids | Zendy

Chhor Rakeshwar B. | Zendy; Nosse Bernd | Zendy; Sörgel Sebastian | Zendy; Böhm Claudius | Zendy; Seitz Michael | Zendy; Reiser Oliver | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research