Synthesis of (+) and (-)-Streptomyces coelicolor Butanolide 5 (SCB-5)

被引：2

作者：

Donges, Jonas ^{[1
]}

Hofmann, Sandra ^{[2
]}

Brueggemann, Moritz ^{[3
]}

Frank, Andrea ^{[1
]}

Schollmeyer, Dieter ^{[1
]}

Nubbemeyer, Udo ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Organ Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

[2] Konrad Adenauer Gymnasium, Worthstr 16, D-56457 Westerburg, Germany

[3] Shimadzu Deutschland GmbH, Leuschnerpk 4, D-64347 Griesheim, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 22期

关键词：

Bioactive gamma-butyrolactone; Diastereoselective synthesis; Iodocyclization; Ozonolysis; Zwitterionic aza-Claisen rearrangement; BUTYROLACTONE AUTOREGULATOR RECEPTOR; GAMMA-BUTYROLACTONE; ANTIBIOTIC PRODUCTION; A-FACTOR; STREPTOMYCES-COELICOLOR; VIRGINIAE BUTANOLIDES; CLAISEN REARRANGEMENT; SECONDARY METABOLISM; ASYMMETRIC-SYNTHESIS; MICROBIAL CHEMISTRY;

D O I：

10.1002/ejoc.202100497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3345 / 3358

页数：14

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