Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue

Gunda I. Georg; Syed M. Ali; Thomas C. Boge; Apurba Datta; Lise Falborg; Richard H. Himes

doi:10.1016/0040-4039(94)88392-0

Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue

Gunda I. Georg, Syed M. Ali, Thomas C. Boge, Apurba Datta, Lise Falborg, Richard H. Himes

Medicinal Chemistry

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Abstract

Hydrolytic procedures for selective 2-debenzoylation and 2,4-dideacylation of 2′-O-tert-butyldimethylsilyl-7-O-(triethylsilyl)taxol are reported. The first synthesis and biological evaluation of a 4-substituted analogue, 4-deacetyl-4-isobutanoyltaxol, is presented. The chemistry described in this letter is suitable for the facile synthesis of taxol congeners modified at C-2 and/or C-4.

Original language	English (US)
Pages (from-to)	8931-8934
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	48
DOIs	https://doi.org/10.1016/0040-4039(94)88392-0
State	Published - Nov 28 1994

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title = "Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue",

abstract = "Hydrolytic procedures for selective 2-debenzoylation and 2,4-dideacylation of 2′-O-tert-butyldimethylsilyl-7-O-(triethylsilyl)taxol are reported. The first synthesis and biological evaluation of a 4-substituted analogue, 4-deacetyl-4-isobutanoyltaxol, is presented. The chemistry described in this letter is suitable for the facile synthesis of taxol congeners modified at C-2 and/or C-4.",

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T1 - Selective C-2 and C-4 deacylation and acylation of taxol

T2 - The first synthesis of a C-4 substituted taxol analogue

AU - Georg, Gunda I.

AU - Ali, Syed M.

AU - Boge, Thomas C.

AU - Datta, Apurba

AU - Falborg, Lise

AU - Himes, Richard H.

PY - 1994/11/28

Y1 - 1994/11/28

N2 - Hydrolytic procedures for selective 2-debenzoylation and 2,4-dideacylation of 2′-O-tert-butyldimethylsilyl-7-O-(triethylsilyl)taxol are reported. The first synthesis and biological evaluation of a 4-substituted analogue, 4-deacetyl-4-isobutanoyltaxol, is presented. The chemistry described in this letter is suitable for the facile synthesis of taxol congeners modified at C-2 and/or C-4.

AB - Hydrolytic procedures for selective 2-debenzoylation and 2,4-dideacylation of 2′-O-tert-butyldimethylsilyl-7-O-(triethylsilyl)taxol are reported. The first synthesis and biological evaluation of a 4-substituted analogue, 4-deacetyl-4-isobutanoyltaxol, is presented. The chemistry described in this letter is suitable for the facile synthesis of taxol congeners modified at C-2 and/or C-4.

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue

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