Synthetic studies with 13-deoxybaccatin III

Yu Mi Ahn; David G. Vander Velde; Gunda I. Georg

doi:10.1021/jo011183q

Synthetic studies with 13-deoxybaccatin III

Yu Mi Ahn, David G. Vander Velde, Gunda I. Georg

Medicinal Chemistry

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

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Abstract

An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI₂, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.

Original language	English (US)
Pages (from-to)	7140-7143
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	67
Issue number	20
DOIs	https://doi.org/10.1021/jo011183q
State	Published - Oct 4 2002

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title = "Synthetic studies with 13-deoxybaccatin III",

abstract = "An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI2, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.",

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year = "2002",

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T1 - Synthetic studies with 13-deoxybaccatin III

AU - Ahn, Yu Mi

AU - Vander Velde, David G.

AU - Georg, Gunda I.

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N2 - An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI2, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.

AB - An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI2, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.

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JO - Journal of Organic Chemistry

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Synthetic studies with 13-deoxybaccatin III

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