Synthesis of optically active polycyclic compounds by Diels-Alder reactions of (+)-nopadiene

Lucio Minuti, Aldo Taticchi, Assunta Marrocchi, Alessandra Broggi, E. Gács-Baitz

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

4-Oxo-2-cyclopentenylacetate 1 underwent a tandem Diels-Alder reaction with (+)-nopadiene 3 to lead to C 2-symmetric optically active polycyclic ketone 4. All attempts to carry out similar processes with acetoxy ketone 1 and two different dienes, that is, (+)-nopadiene 3 and isoprene 6 or 2,3-dimethyl-1,3-butadiene 7 were unsuccessful. Enantiomerically pure polycyclic ketones 8 and 9 were prepared by Diels-Alder cycloaddition between optically active α,β-unsaturated ketone 5 and dienes 6 and 7.

Original languageEnglish
Pages (from-to)3245-3248
Number of pages4
JournalTetrahedron Asymmetry
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 18 2004

Fingerprint

Polycyclic Compounds
Diels-Alder reactions
Cycloaddition Reaction
Ketones
ketones
dienes
synthesis
Isoprene
Cycloaddition
cycloaddition
butadiene
Butadiene

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of optically active polycyclic compounds by Diels-Alder reactions of (+)-nopadiene. / Minuti, Lucio; Taticchi, Aldo; Marrocchi, Assunta; Broggi, Alessandra; Gács-Baitz, E.

In: Tetrahedron Asymmetry, Vol. 15, No. 20, 18.10.2004, p. 3245-3248.

Research output: Contribution to journalArticle

Minuti, Lucio ; Taticchi, Aldo ; Marrocchi, Assunta ; Broggi, Alessandra ; Gács-Baitz, E. / Synthesis of optically active polycyclic compounds by Diels-Alder reactions of (+)-nopadiene. In: Tetrahedron Asymmetry. 2004 ; Vol. 15, No. 20. pp. 3245-3248.
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