Asymmetric total synthesis of cryptoconcatone I. Issue 14 (22nd March 2019)

• Record Type: Journal Article
• Authors: Acharyya, Ranjan Kumar; Pal, Pratik; Chatterjee, Shrestha; Nanda, Samik
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 14(2019)
• Page Start: 3552
• Page End: 3566
• Publication Date: 2019-03-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00399a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient asymmetric total synthesis of naturally occurring γ- Z -butenolide cryptoconcatone I was achieved by employing substrate-directed reductive epoxide ring opening and late-stage "Pd–Cu" catalyzed cascade cyclization. Abstract : Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ- Z -butenolide framework, is described here for the first time. Asymmetric propargylation, E -selective cross metathesis, and regioselective reductive epoxide ring opening were employed to access the enantiopure terminal alkyne. Late stage bimetallic cascade cyclization of the alkyne with ( Z )-3-bromoacrylic acid afforded the natural product in an efficient way.