Aarhus University Seal / Aarhus Universitets segl

Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avisLetterForskningpeer review

Standard

Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**. / Wørmer, Gustav J.; Villadsen, Nikolaj L.; Nørby, Peter; Poulsen, Thomas B.

I: Angewandte Chemie - International Edition, Bind 60, Nr. 19, 05.2021, s. 10521-10525.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avisLetterForskningpeer review

Harvard

Wørmer, GJ, Villadsen, NL, Nørby, P & Poulsen, TB 2021, 'Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**', Angewandte Chemie - International Edition, bind 60, nr. 19, s. 10521-10525. https://doi.org/10.1002/anie.202101439

APA

Wørmer, G. J., Villadsen, N. L., Nørby, P., & Poulsen, T. B. (2021). Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**. Angewandte Chemie - International Edition, 60(19), 10521-10525. https://doi.org/10.1002/anie.202101439

CBE

Wørmer GJ, Villadsen NL, Nørby P, Poulsen TB. 2021. Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**. Angewandte Chemie - International Edition. 60(19):10521-10525. https://doi.org/10.1002/anie.202101439

MLA

Vancouver

Wørmer GJ, Villadsen NL, Nørby P, Poulsen TB. Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**. Angewandte Chemie - International Edition. 2021 maj;60(19):10521-10525. https://doi.org/10.1002/anie.202101439

Author

Wørmer, Gustav J. ; Villadsen, Nikolaj L. ; Nørby, Peter ; Poulsen, Thomas B. / Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**. I: Angewandte Chemie - International Edition. 2021 ; Bind 60, Nr. 19. s. 10521-10525.

Bibtex

@article{cae38aeb48c74c868f905e5212145ee7,
title = "Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**",
abstract = "Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.",
keywords = "asymmetric catalysis, electrophile, natural products, total synthesis, transition metal catalysis",
author = "W{\o}rmer, {Gustav J.} and Villadsen, {Nikolaj L.} and Peter N{\o}rby and Poulsen, {Thomas B.}",
note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",
year = "2021",
month = may,
doi = "10.1002/anie.202101439",
language = "English",
volume = "60",
pages = "10521--10525",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH",
number = "19",

}

RIS

TY - JOUR

T1 - Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

AU - Wørmer, Gustav J.

AU - Villadsen, Nikolaj L.

AU - Nørby, Peter

AU - Poulsen, Thomas B.

N1 - Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/5

Y1 - 2021/5

N2 - Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

AB - Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

KW - asymmetric catalysis

KW - electrophile

KW - natural products

KW - total synthesis

KW - transition metal catalysis

UR - http://www.scopus.com/inward/record.url?scp=85102997715&partnerID=8YFLogxK

U2 - 10.1002/anie.202101439

DO - 10.1002/anie.202101439

M3 - Letter

C2 - 33576128

AN - SCOPUS:85102997715

VL - 60

SP - 10521

EP - 10525

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 19

ER -