The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.

G Appendino; A Noncovich; P Bettoni; P Dambruoso; Olov Sterner; G Fontana; E Bombardelli

doi:10.1002/ejoc.200300376

The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.

G Appendino, A Noncovich, P Bettoni, P Dambruoso, Olov Sterner, G Fontana, E Bombardelli

Centre for Analysis and Synthesis

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

Abstract

The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Original language	English
Pages (from-to)	4422-4431
Journal	European Journal of Organic Chemistry
Volume	2003
Issue number	22
DOIs	https://doi.org/10.1002/ejoc.200300376
Publication status	Published - 2003

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

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10.1002/ejoc.200300376

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title = "The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.",

abstract = "The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. ({\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)",

author = "G Appendino and A Noncovich and P Bettoni and P Dambruoso and Olov Sterner and G Fontana and E Bombardelli",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2003",

doi = "10.1002/ejoc.200300376",

language = "English",

volume = "2003",

pages = "4422--4431",

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TY - JOUR

T1 - The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.

AU - Appendino, G

AU - Noncovich, A

AU - Bettoni, P

AU - Dambruoso, P

AU - Sterner, Olov

AU - Fontana, G

AU - Bombardelli, E

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2003

Y1 - 2003

N2 - The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

AB - The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

U2 - 10.1002/ejoc.200300376

DO - 10.1002/ejoc.200300376

M3 - Article

SN - 1434-193X

VL - 2003

SP - 4422

EP - 4431

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 22

ER -

The reductive fragmentation of 7-hydroxy-9,10-dioxotaxoids.

Abstract

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