Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8076
Authors: Donges, Jonas
Hofmann, Sandra
Brüggemann, Moritz
Frank, Andrea
Schollmeyer, Dieter
Nubbemeyer, Udo
Title: Synthesis of (+) and (-)-Streptomyces coelicolor butanolide 5 (SCB-5)
Online publication date: 11-Nov-2022
Year of first publication: 2021
Language: english
Abstract: Various 1-(1-hydroxyalkyl) paraconyl alcohols are important signaling molecules within antibiotics production in Streptomyces sp. Intending developing a flexible convergent chemical synthesis of such butanolides, a zwitterionic aza-Claisen rearrangement was chosen as reliable strategy generating the central stereotriad. Reaction of enantiopure N-allyl pyrrolidines and 4-phenylbutenoic acid fluoride delivered defined configured amides displaying the 2,3,1’ stereotriads. The configuration was determined by the allyl alcohol moiety indicating a complete remote stereo control. Amide removal by iodolactonization and proceeding reductions, halocyclization and elimination gave key alkylidene tetrahydrofuran derivatives. Stepwise degradation of the olefins through ozonolysis, reductive work-up and protecting group removal delivered both enantiomers of the target Streptomyces coelicolor butanolide 5.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
ROR: https://ror.org/023b0x485
DOI: http://doi.org/10.25358/openscience-8076
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY
Information on rights of use: https://creativecommons.org/licenses/by/4.0/
Journal: European journal of organic chemistry
2021
22
Pages or article number: 3345
3358
Publisher: Wiley VCZ
Publisher place: Weinheim
Issue date: 2021
ISSN: 1099-0690
Publisher DOI: 10.1002/ejoc.202100497
Appears in collections:JGU-Publikationen

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