Synthesis of 7-Deoxypancratistatin from Carbohydrates by the Use of Olefin Metathesis

Anders Eckart Håkansson, Anders Palmelund, H. Holm, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The stereocontrolled synthesis of (+)-7-deoxypancratistatin is described. The convergent synthesis has been achieved by two different strategies, both of which commence from a pentose and piperonal. The latter is converted into allylic bromide 7, which is then coupled with a protected methyl 5-deoxy-5-iodo-D-ribofuranoside in the presence of zinc metal. The first strategy involves a total of only 13 steps from D-ribose and piperonal, but suffers from a low yield in the zinc-mediated reaction between ribofuranoside 9, benzylamine, and bromide 7. The second strategy involves a total of 18 steps from D-xylose and piperonal. The former is converted into ribofuranoside 28, which is coupled with bromide 7 in the presence of zinc, and this is followed by ring-closing olefin metathesis. Subsequent Overman rearrangement, dihydroxylation, and deprotection then affords the natural product.
Original languageEnglish
JournalChemistry-a European Journal
Volume12
Issue number12
Pages (from-to)3243-3253
ISSN0947-6539
DOIs
Publication statusPublished - 2006

Keywords

  • Zinc
  • Carbohydrates
  • Natural products
  • Antitumour agents
  • Olefin metathesis
  • Total synthesis

Fingerprint Dive into the research topics of 'Synthesis of 7-Deoxypancratistatin from Carbohydrates by the Use of Olefin Metathesis'. Together they form a unique fingerprint.

Cite this