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Total synthesis and structural revision of aeruginosin KT608A


Scherer, Manuel; Gademann, Karl (2017). Total synthesis and structural revision of aeruginosin KT608A. Organic Letters, 19(14):3915-3918.

Abstract

The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual D-diepi-Choi core was prepared from tyrosine via C-H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring L-diepi-Choi was proposed, which was synthesized and confirmed to be identical. Based on these findings, revised structures for six additional aeruginosins (KT608B, KT650, GH553, DA495A, DA511 and KB676) are presented.

Abstract

The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual D-diepi-Choi core was prepared from tyrosine via C-H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring L-diepi-Choi was proposed, which was synthesized and confirmed to be identical. Based on these findings, revised structures for six additional aeruginosins (KT608B, KT650, GH553, DA495A, DA511 and KB676) are presented.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Language:English
Date:11 July 2017
Deposited On:22 Aug 2017 17:12
Last Modified:28 Jul 2020 11:11
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.7b01822
PubMed ID:28696116

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