Asymmetric synthesis of (-)-renieramycin T

Org Biomol Chem. 2016 Aug 14;14(30):7334-44. doi: 10.1039/c6ob01064d. Epub 2016 Jul 13.

Abstract

(-)-Renieramycin T, an interesting tetrahydroisoquinolinequinone alkaloid with a novel renieramycin-ecteinascidin mixed framework, is synthesized from the known phenol 16 in 22 steps with 6.2% overall yield. In the convergent route, the key cyclocondensation between the isoquinoline moiety 27 and trisubstituted phenylalaninol 14 is achieved with good selectivity to furnish bistetrahydroisoquinoline 29, which permits a rapid construction of the pentacyclic framework having a fully substituted aromatic A ring.

MeSH terms

  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Isoquinolines / chemistry*
  • Molecular Conformation
  • Phenols / chemistry*
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Tetrahydroisoquinolines / chemical synthesis*
  • Tetrahydroisoquinolines / chemistry

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Isoquinolines
  • Phenols
  • Tetrahydroisoquinolines
  • phenylalaninol
  • Phenylalanine
  • isoquinoline