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

doi:10.1021/ol016411h

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 journal › Article (Academic Journal) › peer-review

31 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 language	English
Pages (from-to)	3005-3008
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	19
DOIs	https://doi.org/10.1021/ol016411h
Publication status	Published - 20 Sep 2001

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

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.",

author = "Booker-Milburn, {Kevin I.} and Dudin, {Leo F.} and Anson, {Christopher E.} and Guile, {Simon D.}",

year = "2001",

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language = "English",

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journal = "Organic Letters",

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T1 - Formal intramolecular [5 + 2] photocycloaddition reactions of maleimides

T2 - A novel approach to the CDE ring skeleton of (-)-cephalotaxine

AU - Booker-Milburn, Kevin I.

AU - Dudin, Leo F.

AU - Anson, Christopher E.

AU - Guile, Simon D.

PY - 2001/9/20

Y1 - 2001/9/20

N2 - 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.

AB - 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.

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U2 - 10.1021/ol016411h

DO - 10.1021/ol016411h

M3 - Article (Academic Journal)

C2 - 11554829

AN - SCOPUS:0035922371

VL - 3

SP - 3005

EP - 3008

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 19

ER -

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

Abstract

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