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

Research output: Contribution to journalArticle

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.
LanguageUndefined/Unknown
Pages8553-8556
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number52
DOIs
Publication statusPublished - 1993

Keywords

  • cyclizations
  • vinyl sulfones
  • perhydroazulenes
  • trans-hydrindanes

Cite this

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title = "Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes",
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.",
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author = "Jones, {D. Neville} and Maybury, {Mark W. J.} and Steven Swallow and Tomkinson, {Nicholas C. O.}",
year = "1993",
doi = "10.1016/S0040-4039(00)61383-7",
language = "Undefined/Unknown",
volume = "34",
pages = "8553--8556",
journal = "Tetrahedron Letters",
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Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes. / Jones, D. Neville; Maybury, Mark W. J.; Swallow, Steven; Tomkinson, Nicholas C. O.

In: Tetrahedron Letters, Vol. 34, No. 52, 1993, p. 8553-8556.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes

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

VL - 34

SP - 8553

EP - 8556

JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -