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

[img] Text
Gn-gi_et_al-2019-Chemistry_-_A_European_Journal.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (880kB)
[img] Text
Brefeldin_ChemXriv_subm.docx - Accepted Version
Available under License Publisher holds Copyright.

Download (1MB)
[img]
Preview
Text
Brefeldin_boris.pdf - Accepted Version
Available under License Publisher holds Copyright.

Download (763kB) | Preview

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 > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Gnägi, Lars, Martz, Severin Vital, Meyer, Daniel, Schärer, Robin Marc, 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:

05 Dec 2022 15:35

Publisher DOI:

10.1002/chem.201903392

BORIS DOI:

10.7892/boris.138853

URI:

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

Actions (login required)

Edit item Edit item
Provide Feedback