Total Synthesis of (–)‐Heliespirone A and (+)‐Heliespirone C. Issue 23 (2nd July 2014)

• Record Type: Journal Article
• Authors: Norcott, Philip; McErlean, Christopher S. P.
• Is Part Of: European journal of organic chemistry. Issue 23(2014)
• Page Start: 5056
• Page End: 5062
• Publication Date: 2014-07-02
• Subjects: Total synthesis -- Natural products -- Asymmetric synthesis -- Sigmatropic rearrangement -- Michael addition -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402420
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Total syntheses of the spiro‐epimeric natural products (–)‐heliespirone A and (+)‐heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa‐Michael addition. Abstract : Total syntheses of the epimeric natural products (–)‐heliespirone A and (+)‐heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa‐Michael addition.