Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine

Chen Wei Lin, Sin Wei Liu, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of S N2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.

Original languageEnglish
Pages (from-to)5292-5299
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number32
DOIs
StatePublished - 28 Aug 2013

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