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

Publication: Research - peer-reviewJournal article – Annual report year: 2006

View graph of relations

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
Publication date2006
Volume12
Issue12
Pages3243-3253
ISSN0947-6539
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 24

Keywords

  • Zinc, Carbohydrates, Natural products, Antitumour agents, Olefin metathesis, Total synthesis
Download as:
Download as PDF
Select render style:
APAAuthorCBEHarvardMLAStandardVancouverShortLong
PDF
Download as HTML
Select render style:
APAAuthorCBEHarvardMLAStandardVancouverShortLong
HTML
Download as Word
Select render style:
APAAuthorCBEHarvardMLAStandardVancouverShortLong
Word

ID: 2688690