A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Ruben L. H. Andringa; Niels A. W. de Kok; Arnold J. M. Driessen; Adriaan J. Minnaard

doi:10.1002/anie.202104759

A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Ruben L. H. Andringa, Niels A. W. de Kok, Arnold J. M. Driessen, Adriaan J. Minnaard^*

^*Corresponding author for this work

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

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Abstract

Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

Original language	English
Pages (from-to)	17497-17503
Number of pages	7
Journal	Angewandte Chemie (International ed. in English)
Volume	60
Issue number	32
Early online date	30-Apr-2021
DOIs	https://doi.org/10.1002/anie.202104759
Publication status	Published - 2-Aug-2021

Keywords

Archaea
asymmetric hydrogenation
lipids
membrane spanning
metathesis

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10.1002/anie.202104759Licence: CC BY-NC-ND

A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide Final publisher's version, 1.48 MBLicence: CC BY-NC-ND

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title = "A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide",

abstract = "Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.",

keywords = "Archaea, asymmetric hydrogenation, lipids, membrane spanning, metathesis",

author = "Andringa, {Ruben L. H.} and {de Kok}, {Niels A. W.} and Driessen, {Arnold J. M.} and Minnaard, {Adriaan J.}",

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T1 - A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

AU - Andringa, Ruben L. H.

AU - de Kok, Niels A. W.

AU - Driessen, Arnold J. M.

AU - Minnaard, Adriaan J.

PY - 2021/8/2

Y1 - 2021/8/2

N2 - Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

AB - Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

KW - Archaea

KW - asymmetric hydrogenation

KW - lipids

KW - membrane spanning

KW - metathesis

U2 - 10.1002/anie.202104759

DO - 10.1002/anie.202104759

M3 - Article

C2 - 33929790

SN - 1433-7851

VL - 60

SP - 17497

EP - 17503

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

IS - 32

ER -

A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Abstract

Keywords

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