Total Synthesis of dl-Ancistrofuran: A Study of Cyclic Ether Formation

Thomas R Hoye, Andrew J. Caruso

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A six-step synthesis of dl-ancistrofuran (1) and its C-2 epimer (31) which involves a mercuric ion initiated diene cyclization of homogeranic acid to give lactone 16 and the phenylselenenyl chloride induced cyclization of alkylidene lactone 19 has been achieved. Also of interest are the zinc chloride assisted aldol condensation of 17 with α-(phenylthio)-γ-butyrolactone enolate anion to generate 29 and the use of ene adducts of 27 as substrates for cyclization to tetrahydrofurans 25 and 26.

Original languageEnglish (US)
Pages (from-to)1198-1205
Number of pages8
JournalJournal of Organic Chemistry
Volume46
Issue number6
DOIs
StatePublished - Mar 1981

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