Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the red sea sponge toxiclona toxius

Sara Isaacs; Yoel Kashman

doi:10.1016/0040-4039(92)88184-7

Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the red sea sponge toxiclona toxius

Sara Isaacs^*, Yoel Kashman

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

Two hexaprenylhydroquinone derived disulfates, shaagrockol B and C (1 and 2) were isolated from the Red Sea sponge Toxiclona toxius (Levi, 1958). The structure of these two new hexaprenoid, antifungal metabolites was determined by spectroscopic methods, mainly 2D-NMR measurements as well as chemical modifications. Ozonolysis of compound 2 afforded compound 1 and the acid catalysed rearrangement of 1, leading to compounds 3 and 4, has been elucidated.

Original language	English
Pages (from-to)	2227-2230
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	16
DOIs	https://doi.org/10.1016/0040-4039(92)88184-7
State	Published - 14 Apr 1992

Keywords

NMR
antifungal
hexaprenylhydroquinone
sponge
sulfate

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N2 - Two hexaprenylhydroquinone derived disulfates, shaagrockol B and C (1 and 2) were isolated from the Red Sea sponge Toxiclona toxius (Levi, 1958). The structure of these two new hexaprenoid, antifungal metabolites was determined by spectroscopic methods, mainly 2D-NMR measurements as well as chemical modifications. Ozonolysis of compound 2 afforded compound 1 and the acid catalysed rearrangement of 1, leading to compounds 3 and 4, has been elucidated.

AB - Two hexaprenylhydroquinone derived disulfates, shaagrockol B and C (1 and 2) were isolated from the Red Sea sponge Toxiclona toxius (Levi, 1958). The structure of these two new hexaprenoid, antifungal metabolites was determined by spectroscopic methods, mainly 2D-NMR measurements as well as chemical modifications. Ozonolysis of compound 2 afforded compound 1 and the acid catalysed rearrangement of 1, leading to compounds 3 and 4, has been elucidated.

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KW - antifungal

KW - hexaprenylhydroquinone

KW - sponge

KW - sulfate

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Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the red sea sponge toxiclona toxius

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Keywords

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