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  1. Article ; Online: Development of the Synthesis of Desepoxy-Tedanolide C.

    Lücke, Daniel / Kalesse, Markus

    The Journal of organic chemistry

    2024  Volume 89, Issue 4, Page(s) 2408–2430

    Abstract: We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. ...

    Abstract We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. Key steps of the synthesis are a Kiyooka aldol reaction that builds up the tertiary alcohol flanked by three oxygenated carbon atoms and two aldol reactions used for fragment couplings. A Julia-Kocienski olefination was used for installation of the side chain. Besides the successful synthesis, the development for the protecting group setup of the southwestern hemisphere is described in detail as well as another retrosynthetic attempt for building up the target molecule.
    Language English
    Publishing date 2024-01-25
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.3c02437
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  2. Article ; Online: Stereoselective Construction of β-chiral Homoallyl Functionalities by Substrate- and Reagent-Controlled Iterative 1,2-Metallate Rearrangements.

    Linne, Elvira / Kalesse, Markus

    Organic letters

    2023  Volume 25, Issue 46, Page(s) 8210–8214

    Abstract: Homoallylic alcohols possessing chiral β-centers are considered highly valuable in the synthesis of polyketide-based natural products. Therefore, there is a significant demand for new methods that allow for their stereoselective access. In pursuit of ... ...

    Abstract Homoallylic alcohols possessing chiral β-centers are considered highly valuable in the synthesis of polyketide-based natural products. Therefore, there is a significant demand for new methods that allow for their stereoselective access. In pursuit of this objective, we have successfully combined our substrate-controlled protocol of Hoppe-Matteson-Aggarwal chemistry with iterative 1,2-metallate rearrangements. Notably, this approach has proven effective in introducing not only primary alcohols but also other functional groups such as alkynes and protected amines.
    Language English
    Publishing date 2023-11-09
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c02935
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Synthesis of Desepoxy-Tedanolide C.

    Lücke, Daniel / Kalesse, Markus

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 24, Page(s) 7085–7089

    Abstract: The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and ... ...

    Abstract The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia-Kocienski olefination were used to assemble the carbon framework.
    Language English
    Publishing date 2021-04-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202100553
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  4. Article ; Online: Total Synthesis of Acanthodoral Using a Rearrangement Strategy.

    Eggert, Alina / Schuppe, Karl T / Fuchs, Hazel L S / Brönstrup, Mark / Kalesse, Markus

    Organic letters

    2024  Volume 26, Issue 15, Page(s) 2893–2896

    Abstract: We present the second total synthesis of (±)-acanthodoral, a sesquiterpenoid derived from the marine ... ...

    Abstract We present the second total synthesis of (±)-acanthodoral, a sesquiterpenoid derived from the marine nudibranch
    Language English
    Publishing date 2024-01-02
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c03717
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Asymmetric Total Synthesis of Illisimonin A.

    Etling, Christoph / Tedesco, Giada / Di Marco, Anna / Kalesse, Markus

    Journal of the American Chemical Society

    2023  Volume 145, Issue 12, Page(s) 7021–7029

    Abstract: The discovery of illisimonin A in 2017 extended the structural repertoire of ... ...

    Abstract The discovery of illisimonin A in 2017 extended the structural repertoire of the
    Language English
    Publishing date 2023-03-16
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c01262
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

    Z 4' 55/32: Show issues
    Z 7.3: Show issues

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  6. Article ; Online: Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation.

    Linne, Yannick / Lücke, Daniel / Gerdes, Kjeld / Bajerke, Kevin / Kalesse, Markus

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 30, Issue 3, Page(s) e202302699

    Abstract: Allylic alcohols are a privileged motif in natural product synthesis and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that chiral acetonide-protected polyketide fragments performing the ... ...

    Abstract Allylic alcohols are a privileged motif in natural product synthesis and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that chiral acetonide-protected polyketide fragments performing the Hoppe-Matteson-Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities rendering this protocol a highly valuable alternative to the Nozaki-Hiyama-Takai-Kishi reaction. Various stereodyads and -triads were investigated to determine their substrate induction. The mostly strong inherent stereoinduction was attributed to a combination of steric and electronic effects.
    Language English
    Publishing date 2023-11-22
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202302699
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Ekkehard Winterfeldt (1932-2014).

    Kalesse, Markus

    Angewandte Chemie (International ed. in English)

    2015  Volume 54, Issue 1, Page(s) 35

    Abstract: Ekkehard Winterfeldt, who was President of the Gesellschaft Deutscher Chemiker (German Chemical Society; GDCh) from 1996-1997 passed away on October 11, 2014. His research achievements included the synthesis of alkaloids and steroids, and stereoselective ...

    Abstract Ekkehard Winterfeldt, who was President of the Gesellschaft Deutscher Chemiker (German Chemical Society; GDCh) from 1996-1997 passed away on October 11, 2014. His research achievements included the synthesis of alkaloids and steroids, and stereoselective transformations. He was known as a gentleman and an inspiring scholar, and was able to convey his passion for science to everybody who worked with him.
    Language English
    Publishing date 2015-01-02
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201410838
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  8. Article ; Online: Towards the total synthesis of chondrochloren A

    Geldsetzer, Jan / Kalesse, Markus

    16 ; 670 ; 673 ; Beilstein journal of organic chemistry ; Germany

    synthesis of the (Z)-enamide fragment.

    2022  

    Abstract: The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was ... ...

    Abstract The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N'-dimethylethane-1,2-diamine.
    Keywords Z-enamide ; cross coupling ; myxobacteria ; natural product ; ribolactone
    Language English
    Publishing date 2022-05-06
    Publishing country de
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  9. Article: Chiral Polyoxygenated Tertiary Alcohols through Kiyooka Aldol Reaction

    Lücke, Daniel / Kalesse, Markus

    Synlett

    2022  Volume 33, Issue 12, Page(s) 1117–1122

    Abstract: Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology ... ...

    Abstract Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simple aromatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the α- and/or β-position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural products are presented. 1

    Introduction 2

    Scope of the Reaction 3

    Synthetic Applications 4

    Conclusion
    Keywords aldol reaction ; tertiary alcohols ; ketene acetal ; stereoselective synthesis ; double-bond geometry
    Language English
    Publishing date 2022-02-17
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2042012-2
    ISSN 1437-2096 ; 0936-5214
    ISSN (online) 1437-2096
    ISSN 0936-5214
    DOI 10.1055/a-1775-7590
    Database Thieme publisher's database

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  10. Article: Towards the total synthesis of chondrochloren A: synthesis of the (

    Geldsetzer, Jan / Kalesse, Markus

    Beilstein journal of organic chemistry

    2020  Volume 16, Page(s) 670–673

    Abstract: The stereoselective synthesis of the ( ...

    Abstract The stereoselective synthesis of the (
    Language English
    Publishing date 2020-04-14
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.16.64
    Database MEDical Literature Analysis and Retrieval System OnLINE

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