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 |
Files in This Item:
File | Description | Size | Format | ||
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synthesis_of__and_streptomyce-20221111103532559.pdf | 708.11 kB | Adobe PDF | View/Open |