The Total Synthesis of (±)‐Fumimycin | Zendy

Gross Patrick J. | Zendy; Bräse Stefan | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

The Total Synthesis of (±)‐Fumimycin

Author(s) -

Gross Patrick J.,

Bräse Stefan

Publication year - 2010

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201001036

Subject(s) - total synthesis , chemistry , isomerization , aldehyde , oxime , claisen rearrangement , natural product , amine gas treating , combinatorial chemistry , stereochemistry , catalysis , organic chemistry

The antibiotic agent fumimycin has been synthesized for the first time. This natural product was found to inhibit the bacterial peptide deformylase and may represent a lead structure to a class of novel antibacterials. Our synthetic strategy towards fumimycin involved the following steps: Dakin oxidation of an aldehyde functionality, conversion of an oxime through radical fragmentation to form an N ‐diphenylphosphoryl group, construction of an α‐trisubstituted amine by 1,2‐addition to a ketimine, a Claisen rearrangement with subsequent transition‐metal‐catalyzed olefin isomerization to install a propenyl chain and final amidation.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research