Gutenberg Open Science: Synthesis of (+) and (-)-Streptomyces coelicolor butanolide 5 (SCB-5)

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8076

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DC Field	Value	Language
dc.contributor.author	Donges, Jonas	-
dc.contributor.author	Hofmann, Sandra	-
dc.contributor.author	Brüggemann, Moritz	-
dc.contributor.author	Frank, Andrea	-
dc.contributor.author	Schollmeyer, Dieter	-
dc.contributor.author	Nubbemeyer, Udo	-
dc.date.accessioned	2022-11-11T09:34:55Z	-
dc.date.available	2022-11-11T09:34:55Z	-
dc.date.issued	2021	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/8091	-
dc.description.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.	en_GB
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/	*
dc.subject.ddc	540 Chemie	de_DE
dc.subject.ddc	540 Chemistry and allied sciences	en_GB
dc.title	Synthesis of (+) and (-)-Streptomyces coelicolor butanolide 5 (SCB-5)	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-8076	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	European journal of organic chemistry	de
jgu.journal.volume	2021	de
jgu.journal.issue	22	de
jgu.pages.start	3345	de
jgu.pages.end	3358	de
jgu.publisher.year	2021	-
jgu.publisher.name	Wiley VCZ	de
jgu.publisher.place	Weinheim	de
jgu.publisher.issn	1099-0690	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/ejoc.202100497	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	JGU-Publikationen

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