Stereoselective synthesis of squalamine dessulfate

Robert M. Moriarty, Livia A. Enache, William A. Kinney, Craig S. Allen, James Canary, Sudersan M. Tuladhar, Liang Guo

Research output: Contribution to journalArticle

Abstract

Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol. The key step in establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-methylbutane to yield the cholesteryl precursors of the epimeric squalamine dessulfates.

Original languageEnglish (US)
Pages (from-to)5139-5142
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number29
DOIs
StatePublished - Jul 17 1995

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Stigmasterol
Stereochemistry
squalamine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Moriarty, R. M., Enache, L. A., Kinney, W. A., Allen, C. S., Canary, J., Tuladhar, S. M., & Guo, L. (1995). Stereoselective synthesis of squalamine dessulfate. Tetrahedron Letters, 36(29), 5139-5142. https://doi.org/10.1016/00404-0399(50)10116-

Stereoselective synthesis of squalamine dessulfate. / Moriarty, Robert M.; Enache, Livia A.; Kinney, William A.; Allen, Craig S.; Canary, James; Tuladhar, Sudersan M.; Guo, Liang.

In: Tetrahedron Letters, Vol. 36, No. 29, 17.07.1995, p. 5139-5142.

Research output: Contribution to journalArticle

Moriarty, RM, Enache, LA, Kinney, WA, Allen, CS, Canary, J, Tuladhar, SM & Guo, L 1995, 'Stereoselective synthesis of squalamine dessulfate', Tetrahedron Letters, vol. 36, no. 29, pp. 5139-5142. https://doi.org/10.1016/00404-0399(50)10116-
Moriarty RM, Enache LA, Kinney WA, Allen CS, Canary J, Tuladhar SM et al. Stereoselective synthesis of squalamine dessulfate. Tetrahedron Letters. 1995 Jul 17;36(29):5139-5142. https://doi.org/10.1016/00404-0399(50)10116-
Moriarty, Robert M. ; Enache, Livia A. ; Kinney, William A. ; Allen, Craig S. ; Canary, James ; Tuladhar, Sudersan M. ; Guo, Liang. / Stereoselective synthesis of squalamine dessulfate. In: Tetrahedron Letters. 1995 ; Vol. 36, No. 29. pp. 5139-5142.
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