Formal intramolecular [5 + 2] photocycloaddition reactions of maleimides: A novel approach to the CDE ring skeleton of (-)-cephalotaxine

Kevin I. Booker-Milburn*, Leo F. Dudin, Christopher E. Anson, Simon D. Guile

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

30 Citations (Scopus)

Abstract

matrix presented A concise approach to the cephalotaxine CDE ring skeleton based on the intramolecular formal [5 + 2] photocycloaddition of cyclopentenyl-substituted maleimides is described. An investigation of the diatereoselectivity afforded by various protected alkoxy groups demonstrated that the best selectivity (3.5:1) was afforded by the free hydroxyl group, strongly suggesting a hydrogen-bonded excited state.

Original languageEnglish
Pages (from-to)3005-3008
Number of pages4
JournalOrganic Letters
Volume3
Issue number19
DOIs
Publication statusPublished - 20 Sep 2001

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