Journal article

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

Abstract:: A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Lewis, W., Shaw, D., & Robertson, J. (2021). Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines. Beilstein Journal of Organic Chemistry, 17, 334–342.

MLA Style

Lewis, W., et al. “Synthesis of Legonmycins A and B, C(7a)-Hydroxylated Bacterial Pyrrolizidines.” Beilstein Journal of Organic Chemistry, vol. 17, Beilstein-Institut, 2021, pp. 334–42.

Chicago Style

Lewis, W, D Shaw, and J Robertson. 2021. “Synthesis of Legonmycins A and B, C(7a)-Hydroxylated Bacterial Pyrrolizidines.” Beilstein Journal of Organic Chemistry 17: 334–42.
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Files:: Lewis_et_al_Synthesis_of_legonmycins.pdf

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Publisher copy:: 10.3762/bjoc.17.31

Authors

+ Lewis, W More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Shaw, D More by this author

Role:: Author

+ Robertson, J More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

Publisher:: Beilstein-Institut
Journal:: Beilstein Journal of Organic Chemistry More from this journal
Volume:: 17
Pages:: 334-342
Publication date:: 2021-02-02
Acceptance date:: 2021-01-19
DOI:: 10.3762/bjoc.17.31
EISSN:: 1860-5397

Language:: English
Keywords:: legonmycin

vinylogous ureas

acyloxypyrroles

FFR

cyanketones

bacterial pyrrolizidines
Pubs id:: 1159778
Local pid:: pubs:1159778
Deposit date:: 2021-02-02

Terms of use

Copyright holder:: Lewis et al.
Copyright date:: 2021
Rights statement:: © 2021 Lewis et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License. Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions.

Licence:: CC Attribution (CC BY)

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