Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes

D. Neville Jones; Mark W. J. Maybury; Steven Swallow; Nicholas C. O. Tomkinson

doi:10.1016/S0040-4039(00)61383-7

Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes

D. Neville Jones, Mark W. J. Maybury, Steven Swallow, Nicholas C. O. Tomkinson

Pure And Applied Chemistry

Research output: Contribution to journal › Article

13 Citations (Scopus)

Abstract

Anionic species formed by treatment of vinyl sulfones with hydridoaluminates were trapped intramolecularly by esters to provide six- and seven-membered cyclic ketosulfones, e.g. I (R = Me, H, Ar = p-tolyl) and II, exemplified by the stereoselective construction of trans-hydrindanes and of perhydroazulenes. This led to formal syntheses of confertin (III) and damsinic acid.

Original language	Undefined/Unknown
Pages (from-to)	8553-8556
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	52
DOIs	https://doi.org/10.1016/S0040-4039(00)61383-7
Publication status	Published - 1993

Keywords

cyclizations
vinyl sulfones
perhydroazulenes
trans-hydrindanes

Cite this

Jones, D. N., Maybury, M. W. J., Swallow, S., & Tomkinson, N. C. O. (1993). Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes. Tetrahedron Letters, 34(52), 8553-8556. https://doi.org/10.1016/S0040-4039(00)61383-7

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AU - Jones, D. Neville

AU - Maybury, Mark W. J.

AU - Swallow, Steven

AU - Tomkinson, Nicholas C. O.

PY - 1993

Y1 - 1993

N2 - Anionic species formed by treatment of vinyl sulfones with hydridoaluminates were trapped intramolecularly by esters to provide six- and seven-membered cyclic ketosulfones, e.g. I (R = Me, H, Ar = p-tolyl) and II, exemplified by the stereoselective construction of trans-hydrindanes and of perhydroazulenes. This led to formal syntheses of confertin (III) and damsinic acid.

AB - Anionic species formed by treatment of vinyl sulfones with hydridoaluminates were trapped intramolecularly by esters to provide six- and seven-membered cyclic ketosulfones, e.g. I (R = Me, H, Ar = p-tolyl) and II, exemplified by the stereoselective construction of trans-hydrindanes and of perhydroazulenes. This led to formal syntheses of confertin (III) and damsinic acid.

KW - cyclizations

KW - vinyl sulfones

KW - perhydroazulenes

KW - trans-hydrindanes

U2 - 10.1016/S0040-4039(00)61383-7

DO - 10.1016/S0040-4039(00)61383-7

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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10.1016/S0040-4039(00)61383-7