Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F

Scott T. Phillips, Matthew D. Shair

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The ritterazine class of natural products comprises 26 compounds - all of which are spiroketal-containing steroidal heterodimers - that inhibit the proliferation of cultured human cancer cell lines with IC50 values in the low nanomolar range. Little is known about their chemistry, cellular target(s), or mechanism(s) of growth inhibition, due primarily to the small amount of material available from natural sources. In this paper we report syntheses of the eastern halves of ritterazines B, F, G, and H and address the energetic and mechanistic aspects of spiroketal equilibration for each. These studies have led to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F, and they have enabled us to propose a quantitative description of the natural distribution of these ritterazine compounds.

Original languageEnglish (US)
Pages (from-to)6589-6598
Number of pages10
JournalJournal of the American Chemical Society
Volume129
Issue number20
DOIs
StatePublished - May 23 2007

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Stereochemistry
Cells
Biological Products
Inhibitory Concentration 50
Cell Line
Growth
ritterazine B
spiroketal
Neoplasms

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F",
abstract = "The ritterazine class of natural products comprises 26 compounds - all of which are spiroketal-containing steroidal heterodimers - that inhibit the proliferation of cultured human cancer cell lines with IC50 values in the low nanomolar range. Little is known about their chemistry, cellular target(s), or mechanism(s) of growth inhibition, due primarily to the small amount of material available from natural sources. In this paper we report syntheses of the eastern halves of ritterazines B, F, G, and H and address the energetic and mechanistic aspects of spiroketal equilibration for each. These studies have led to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F, and they have enabled us to propose a quantitative description of the natural distribution of these ritterazine compounds.",
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Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5-spiroketal stereochemistry of ritterazines B and F. / Phillips, Scott T.; Shair, Matthew D.

In: Journal of the American Chemical Society, Vol. 129, No. 20, 23.05.2007, p. 6589-6598.

Research output: Contribution to journalArticle

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