Enantioselective Total Synthesis of (-)-Spiroxins A, C, and D

Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18514-18518. doi: 10.1002/anie.202105921. Epub 2021 Jul 13.

Abstract

Spiroxins A, C, and D are metabolites that have been identified in the marine fungal strain LL-37H248. Their unique polycyclic structures and intriguing biological activities make them attractive targets for the synthetic community. Based on a scalable enantioselective epoxidation of 5-substituted naphthoquinone, an oxidation/spiroketalization cascade, ortho-selective chlorination of the phenol unit, and oxime-ester-directed acetoxylation, an enantioselective total synthesis of (-)-spiroxins A and C and the first total synthesis of (-)-spiroxin D have been achieved.

Keywords: core skeleton; enantioselective epoxidation; natural products; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Naphthalenes
  • Spiro Compounds
  • spiroxin C