Asymmetric Total Synthesis of (–)‐Gracilamine Using a Bioinspired Approach. Issue 45 (30th November 2017)

• Record Type: Journal Article
• Authors: Chandra, Atish; Verma, Prachi; Negel, Animesh; Pandey, Ganesh
• Is Part Of: European journal of organic chemistry. Issue 45(2017)
• Page Start: 6788
• Page End: 6792
• Publication Date: 2017-11-30
• Subjects: Alkaloids -- Asymmetric synthesis -- Cycloaddition -- Natural products -- Total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701474
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The asymmetric total synthesis of optically pure (–)‐gracilamine (1 ) was achieved by employing a bioinspired approach. The strategy involved elaboration of 3 a ‐arylhexahydroindole7, a designed precursor, to 3 a ‐formylarylhexahydroindole5, which upon heating withl ‐leucine ethyl ester gave (–)‐1 efficiently. Abstract : An efficient route to the asymmetric total synthesis of optically pure (–)‐gracilamine is achieved through an exo ‐face‐selective ring opening of an aryl‐substituted 7‐aza‐bicyclic heptenesulfone and a bioinspired approach in an advance stage. Boc = tert ‐butoxycarbonyl.