1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

Ian Paterson; Gordon John Florence; Oscar Delgado; Isabelle Lyothier; Jeremy P. Scott; Natascha Sereinig

doi:10.1021/ol0270780

1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

Ian Paterson, Gordon John Florence, Oscar Delgado, Isabelle Lyothier, Jeremy P. Scott, Natascha Sereinig

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Abstract

By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C-1-C-5, C-9-C-16, and C-17-C-24 subunits.

Original language	English
Pages (from-to)	35-38
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	1
DOIs	https://doi.org/10.1021/ol0270780
Publication status	Published - 9 Jan 2003

Keywords

GRAM-SCALE SYNTHESIS
STEREOCONTROLLED SYNTHESIS
(-)-DISCODERMOLIDE
DISCODERMOLIDE
OXIDATION
KETONES
AGENT
MICROTUBULES
ALDEHYDES
MOLECULES

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title = "1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide",

abstract = "By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C-1-C-5, C-9-C-16, and C-17-C-24 subunits.",

keywords = "GRAM-SCALE SYNTHESIS, STEREOCONTROLLED SYNTHESIS, (-)-DISCODERMOLIDE, DISCODERMOLIDE, OXIDATION, KETONES, AGENT, MICROTUBULES, ALDEHYDES, MOLECULES",

author = "Ian Paterson and Florence, \{Gordon John\} and Oscar Delgado and Isabelle Lyothier and Scott, \{Jeremy P.\} and Natascha Sereinig",

year = "2003",

month = jan,

day = "9",

doi = "10.1021/ol0270780",

language = "English",

volume = "5",

pages = "35--38",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "1",

}

TY - JOUR

T1 - 1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

AU - Paterson, Ian

AU - Florence, Gordon John

AU - Delgado, Oscar

AU - Lyothier, Isabelle

AU - Scott, Jeremy P.

AU - Sereinig, Natascha

PY - 2003/1/9

Y1 - 2003/1/9

N2 - By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C-1-C-5, C-9-C-16, and C-17-C-24 subunits.

AB - By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C-1-C-5, C-9-C-16, and C-17-C-24 subunits.

KW - GRAM-SCALE SYNTHESIS

KW - STEREOCONTROLLED SYNTHESIS

KW - (-)-DISCODERMOLIDE

KW - DISCODERMOLIDE

KW - OXIDATION

KW - KETONES

KW - AGENT

KW - MICROTUBULES

KW - ALDEHYDES

KW - MOLECULES

UR - https://www.scopus.com/pages/publications/0037900065

UR - http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/ol0270780

U2 - 10.1021/ol0270780

DO - 10.1021/ol0270780

M3 - Article

SN - 1523-7060

VL - 5

SP - 35

EP - 38

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

Abstract

Keywords

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