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Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)
Author(s) -
Donges Jonas,
Hofmann Sandra,
Brüggemann Moritz,
Frank Andrea,
Schollmeyer Dieter,
Nubbemeyer Udo
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100497
Subject(s) - chemistry , enantiopure drug , streptomyces coelicolor , moiety , amide , enantiomer , tetrahydrofuran , ozonolysis , streptomyces , alcohol , organic chemistry , stereochemistry , enantioselective synthesis , bacteria , catalysis , biochemistry , genetics , solvent , biology , mutant , gene
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.