Total Synthesis of a Pyrrole Lactone Alkaloid, Longanlactone. Issue 28 (15th August 2014)

• Record Type: Journal Article
• Authors: Reddy, Chada Raji; Reddy, Motatipally Damoder; Dilipkumar, Uredi
• Is Part Of: European journal of organic chemistry. Issue 28(2014)
• Page Start: 6310
• Page End: 6313
• Publication Date: 2014-08-15
• Subjects: Total synthesis -- Alkaloids -- ­Nitrogen heterocycles -- Lactones -- Amino acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402563
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The first asymmetric total synthesis of the natural pyrrole lactone longanlactone has been achieved. The key reactions, a Barbier propargylation and a Paal–Knorr pyrrole synthesis, have provided easy access to the target natural product fromL ‐aspartic acid in six steps and 31 % overall yield. The C‐4 epimer of the natural product and propionyllonganlactone have also been prepared by this strategy. Abstract : The first total synthesis of a new pyrrole lactone alkaloid, longanlactone, along with its C‐4 epimer is achieved from the natural amino acidL ‐aspartic acid with a Barbier‐type propargylation and a Paal–Knorr pyrrole synthesis as key steps.