Carbohydrate carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis

Carina Storm Poulsen, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Methyl 5-deoxy-5-iodo-pentofuranosides are reductively ring-opened and propargylated in a tandem fashion in the presence of zinc. The 1,7-enynes thus obtained are subjected to ring-closing enyne metathesis with catalyst B to produce functionalized 1-vinyl cyclohexenes. By adding BnNH2 to the tandem reaction, an amino group can be introduced in the 1,7-enyne products. Addition of 2-TMS-ethynylcerium(III) chloride after the reductive ring-opening produces the corresponding 1,6-enynes. Further annulation of the product 1,3-dienes can be achieved through a Diels-Alder reaction with good control of stereo chemistry. These procedures constitute efficient methods for rapid carbocyclization and annulation of carbohydrates to produce a variety of functionalized five- and six-membered ring systems.
Original languageEnglish
JournalJournal of organic chemistry
Volume67
Issue number13
Pages (from-to)4441-4449
ISSN0022-3263
Publication statusPublished - 2002

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