A Short Synthesis of (+)‐Brefeldin C through Enantioselective Radical Hydroalkynylation

Gnägi, Lars; Martz, Severin Vital; Meyer, Daniel; Schärer, Robin Marc; Renaud, Philippe (2019). A Short Synthesis of (+)‐Brefeldin C through Enantioselective Radical Hydroalkynylation. Chemistry - a European journal, 25(50), pp. 11646-11649. Wiley-VCH 10.1002/chem.201903392

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A very concise total synthesis of (+)‐brefeldin C starting from 2‐furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight‐step synthesis requires six product purifications and it provides (+)‐brefeldin C in 18 % overall yield.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Gnägi, Lars; Martz, Severin Vital; Meyer, Daniel; Schärer, Robin Marc and Renaud, Philippe

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Franziska Bornhauser-Rufer

Date Deposited:

06 Feb 2020 15:24

Last Modified:

01 Aug 2020 02:30

Publisher DOI:

10.1002/chem.201903392

BORIS DOI:

10.7892/boris.138853

URI:

https://boris.unibe.ch/id/eprint/138853

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