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

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

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...

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Bibliographic Details
Published in:Chemistry : a European journal Vol. 25; no. 50; pp. 11646 - 11649
Main Authors: Gnägi, Lars, Martz, Severin Vital, Meyer, Daniel, Schärer, Robin Marc, Renaud, Philippe
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 06-09-2019
Subjects:
asymmetric synthesis
Chemical synthesis
Chemistry
Cyclopentane
Enantiomers
enantioselectivity
hydroalkynylation
natural product
Natural products
Oxidation
radical reaction
Stereoselectivity
Valence
enantioselectivity
radical reaction
asymmetric synthesis
hydroalkynylation
natural product
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Summary: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. Natural products: A very concise total synthesis of (+)‐brefeldin C starting from 2‐furanylcyclopentene and based on an unprecedented enantioselective radical hydroalkynylation has been achieved (see scheme).
Bibliography:https://doi.org/10.26434/chemrxiv.8397731.v1
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A previous version of this manuscript has been deposited on a preprint server
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201903392