Toward the total synthesis of ansalactam A

Anastasia Hager; Christian A. Kuttruff; Elena Herrero-Gómez; Dirk Trauner

doi:10.1016/j.tetlet.2013.10.104

Toward the total synthesis of ansalactam A

Anastasia Hager, Christian A. Kuttruff, Elena Herrero-Gómez, Dirk Trauner

Chemistry

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

Abstract

Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.

Original language	English (US)
Pages (from-to)	59-62
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.104
State	Published - Jan 1 2014

Keywords

Ansamycins
Evans auxiliary
Natural products
Total synthesis
β-Lactones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.10.104

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title = "Toward the total synthesis of ansalactam A",

abstract = "Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.",

keywords = "Ansamycins, Evans auxiliary, Natural products, Total synthesis, β-Lactones",

author = "Anastasia Hager and Kuttruff, {Christian A.} and Elena Herrero-G{\'o}mez and Dirk Trauner",

note = "Funding Information: A.H. (LMU, M{\"u}nchen) is grateful to SDW (Stiftung der Deutschen Wirtschaft), C.A.K. (LMU, M{\"u}nchen) thanks the Fonds der Chemischen Industrie, both for PhD fellowships. E.H.-G. (LMU, M{\"u}nchen) gratefully acknowledges the Alexander von Humboldt Foundation for a postdoctoral fellowship. Additionally, the authors would like to thank Dr. Albert Schr{\"o}ckender for helpful discussions and assistance with scale up experiments and to Dr. Peter Mayer for X-ray crystallography. ",

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doi = "10.1016/j.tetlet.2013.10.104",

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AU - Hager, Anastasia

AU - Kuttruff, Christian A.

AU - Herrero-Gómez, Elena

AU - Trauner, Dirk

N1 - Funding Information: A.H. (LMU, München) is grateful to SDW (Stiftung der Deutschen Wirtschaft), C.A.K. (LMU, München) thanks the Fonds der Chemischen Industrie, both for PhD fellowships. E.H.-G. (LMU, München) gratefully acknowledges the Alexander von Humboldt Foundation for a postdoctoral fellowship. Additionally, the authors would like to thank Dr. Albert Schröckender for helpful discussions and assistance with scale up experiments and to Dr. Peter Mayer for X-ray crystallography.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.

AB - Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.

KW - Ansamycins

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KW - Total synthesis

KW - β-Lactones

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Toward the total synthesis of ansalactam A

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Keywords

ASJC Scopus subject areas

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