Synthesis of acremines A, B and F and studies on the bisacremines

Nils Winter; Dirk Trauner

doi:10.3762/bjoc.15.219

Synthesis of acremines A, B and F and studies on the bisacremines

Nils Winter, Dirk Trauner

Chemistry

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

Abstract

The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

Original language	English (US)
Pages (from-to)	2271-2276
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.219
State	Published - Sep 23 2019

Keywords

Meroterpenoid
Natural product
Selective oxidation
Total synthesis

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.15.219

Cite this

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title = "Synthesis of acremines A, B and F and studies on the bisacremines",

abstract = "The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.",

keywords = "Meroterpenoid, Natural product, Selective oxidation, Total synthesis",

author = "Nils Winter and Dirk Trauner",

note = "Funding Information: The authors thank Dr. Peter Mayer for X-ray structure analysis. Additionally, we acknowledge the Deutsche Forschungs-gemeinschaft (SFB 749 and CIPSM) for generous funding. Dr. Julius R. Reyes is acknowledged for excellent support with the preparation of this article. Publisher Copyright: {\textcopyright} 2019 Winter and Trauner; licensee Beilstein-Institut. License and terms: see end of document.",

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language = "English (US)",

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AU - Winter, Nils

AU - Trauner, Dirk

N1 - Funding Information: The authors thank Dr. Peter Mayer for X-ray structure analysis. Additionally, we acknowledge the Deutsche Forschungs-gemeinschaft (SFB 749 and CIPSM) for generous funding. Dr. Julius R. Reyes is acknowledged for excellent support with the preparation of this article. Publisher Copyright: © 2019 Winter and Trauner; licensee Beilstein-Institut. License and terms: see end of document.

PY - 2019/9/23

Y1 - 2019/9/23

N2 - The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

AB - The acremines are a family of meroterpenoids isolated from fungi of the genus Acremonium. Here, we present the asymmetric total synthesis of acremine F which hinges on a modestly enantioselective dihydroxylation and a subsequent kinetic resolution via a highly selective asymmetric reduction. Chemoselective oxidation of acremine F gave access to acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature.

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KW - Natural product

KW - Selective oxidation

KW - Total synthesis

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

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Synthesis of acremines A, B and F and studies on the bisacremines

Abstract

Keywords

ASJC Scopus subject areas

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