Palladium-Catalyzed Allylic Substitution for the Synthesis of Pericosines

Cheng Yu Chung, Venkatachalam Angamuthu, Long Shiang Li, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A sequence of vinylalumination of α-substituted aldehydes, ring-closing metathesis (RCM), and palladium-catalyzed allylic substitution was utilized to prepare the biologically active natural products, pericosines, from d-ribose. The anti-adduct of vinylalumination was transformed into pericosine A after RCM, removal of the 4-methoxybenzyl protecting group, and chlorination. The diacetate of the anti-adduct was converted to pericosine C after the palladium-catalyzed, SN2′-type, allylic substitution. However, an unexpected dimeric product was generated in utilizing this approach to prepare pericosine E.

Original languageEnglish
Pages (from-to)1327-1333
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume5
Issue number11
DOIs
StatePublished - 1 Nov 2016

Keywords

  • allylic substitution
  • carbasugar
  • cyclitol
  • palladium
  • vinylalumination

Fingerprint

Dive into the research topics of 'Palladium-Catalyzed Allylic Substitution for the Synthesis of Pericosines'. Together they form a unique fingerprint.

Cite this