Total Synthesis of Anhydrocannabisativene

Thomas R. Bailey, Ravi S. Garigipati, Judith A. Morton, Steven M. Weinreb

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

A stereoselective total synthesis of the macrocyclic spermidine alkaloid anhydrocannabisativene (2) has been executed in approximately 17 steps starting from pentadienylsilane 6. The pivotal step in construction of the tetrahydropyridine ring and for establishing the relative stereochemistry of the alkaloid involved an intramolecular imino Diels∼Alder cycloaddition. An intramolecular sulfonamide alkylation was subsequently used to generate the 13-membered macrocyclic lactam ring of 2.

Original languageEnglish (US)
Pages (from-to)3240-3245
Number of pages6
JournalJournal of the American Chemical Society
Volume106
Issue number11
DOIs
StatePublished - Jan 1 1984

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Alkaloids
Macrocyclic Lactams
Stereochemistry
Spermidine
Cycloaddition
Sulfonamides
Alkylation
Cycloaddition Reaction
Lactams

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Bailey, T. R., Garigipati, R. S., Morton, J. A., & Weinreb, S. M. (1984). Total Synthesis of Anhydrocannabisativene. Journal of the American Chemical Society, 106(11), 3240-3245. https://doi.org/10.1021/ja00323a030
Bailey, Thomas R. ; Garigipati, Ravi S. ; Morton, Judith A. ; Weinreb, Steven M. / Total Synthesis of Anhydrocannabisativene. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 11. pp. 3240-3245.
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Bailey, TR, Garigipati, RS, Morton, JA & Weinreb, SM 1984, 'Total Synthesis of Anhydrocannabisativene', Journal of the American Chemical Society, vol. 106, no. 11, pp. 3240-3245. https://doi.org/10.1021/ja00323a030

Total Synthesis of Anhydrocannabisativene. / Bailey, Thomas R.; Garigipati, Ravi S.; Morton, Judith A.; Weinreb, Steven M.

In: Journal of the American Chemical Society, Vol. 106, No. 11, 01.01.1984, p. 3240-3245.

Research output: Contribution to journalArticle

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Bailey TR, Garigipati RS, Morton JA, Weinreb SM. Total Synthesis of Anhydrocannabisativene. Journal of the American Chemical Society. 1984 Jan 1;106(11):3240-3245. https://doi.org/10.1021/ja00323a030