The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent

Ian Paterson; Gordon John Florence

doi:10.1002/ejoc.200300061

The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent

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

Abstract

Marine organisms provide an important source of natural product diversity with an associated range of significant biological activities. Discodermolide, isolated in microscopic quantities from a deep-water sponge, shares the same microtubule-stabilizing mechanism as Taxol and has a promising antitumor profile. There is, however, a chronic supply problem hampering clinical development and so a practical total synthesis of discodermolide is an important goal. This review highlights the completed total syntheses of discodermolide, focusing on the various methods and strategies employed for achieving stereocontrol and realising the pivotal fragment couplings. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Original language	English
Pages (from-to)	2193-2208
Number of pages	16
Journal	European Journal of Organic Chemistry
Volume	2003
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.200300061
Publication status	Published - Jun 2003

Keywords

antitumor agents
cytotoxic
marine polyketides
total synthesis
tubulin
LACTATE-DERIVED KETONES
MARINE NATURAL-PRODUCTS
PI-FACE SELECTIVITY
MEDIATED ALDOL REACTIONS
GRAM-SCALE SYNTHESIS
MEDIUM RING ETHERS
STEREOSELECTIVE SYNTHESIS
POLYPROPIONATE SYNTHESIS
STEREOCONTROLLED SYNTHESIS
ASYMMETRIC-SYNTHESIS

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/ejoc.200300061

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title = "The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent",

abstract = "Marine organisms provide an important source of natural product diversity with an associated range of significant biological activities. Discodermolide, isolated in microscopic quantities from a deep-water sponge, shares the same microtubule-stabilizing mechanism as Taxol and has a promising antitumor profile. There is, however, a chronic supply problem hampering clinical development and so a practical total synthesis of discodermolide is an important goal. This review highlights the completed total syntheses of discodermolide, focusing on the various methods and strategies employed for achieving stereocontrol and realising the pivotal fragment couplings. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).",

keywords = "antitumor agents, cytotoxic, marine polyketides, total synthesis, tubulin, LACTATE-DERIVED KETONES, MARINE NATURAL-PRODUCTS, PI-FACE SELECTIVITY, MEDIATED ALDOL REACTIONS, GRAM-SCALE SYNTHESIS, MEDIUM RING ETHERS, STEREOSELECTIVE SYNTHESIS, POLYPROPIONATE SYNTHESIS, STEREOCONTROLLED SYNTHESIS, ASYMMETRIC-SYNTHESIS",

author = "Ian Paterson and Florence, {Gordon John}",

year = "2003",

month = jun,

doi = "10.1002/ejoc.200300061",

language = "English",

volume = "2003",

pages = "2193--2208",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "12",

}

TY - JOUR

T1 - The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent

AU - Paterson, Ian

AU - Florence, Gordon John

PY - 2003/6

Y1 - 2003/6

N2 - Marine organisms provide an important source of natural product diversity with an associated range of significant biological activities. Discodermolide, isolated in microscopic quantities from a deep-water sponge, shares the same microtubule-stabilizing mechanism as Taxol and has a promising antitumor profile. There is, however, a chronic supply problem hampering clinical development and so a practical total synthesis of discodermolide is an important goal. This review highlights the completed total syntheses of discodermolide, focusing on the various methods and strategies employed for achieving stereocontrol and realising the pivotal fragment couplings. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

AB - Marine organisms provide an important source of natural product diversity with an associated range of significant biological activities. Discodermolide, isolated in microscopic quantities from a deep-water sponge, shares the same microtubule-stabilizing mechanism as Taxol and has a promising antitumor profile. There is, however, a chronic supply problem hampering clinical development and so a practical total synthesis of discodermolide is an important goal. This review highlights the completed total syntheses of discodermolide, focusing on the various methods and strategies employed for achieving stereocontrol and realising the pivotal fragment couplings. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

KW - antitumor agents

KW - cytotoxic

KW - marine polyketides

KW - total synthesis

KW - tubulin

KW - LACTATE-DERIVED KETONES

KW - MARINE NATURAL-PRODUCTS

KW - PI-FACE SELECTIVITY

KW - MEDIATED ALDOL REACTIONS

KW - GRAM-SCALE SYNTHESIS

KW - MEDIUM RING ETHERS

KW - STEREOSELECTIVE SYNTHESIS

KW - POLYPROPIONATE SYNTHESIS

KW - STEREOCONTROLLED SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

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UR - http://dx.doi.org/10.1002/ejoc.200300061

U2 - 10.1002/ejoc.200300061

DO - 10.1002/ejoc.200300061

M3 - Article

SN - 1434-193X

VL - 2003

SP - 2193

EP - 2208

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent

Abstract

Keywords

UN SDGs

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