Seven-Step Total Synthesis of Sporothriolide.
J Org Chem
; 86(17): 12475-12479, 2021 09 03.
Article
in En
| MEDLINE
| ID: mdl-34423986
ABSTRACT
An enantioselective total synthesis of sporothriolide, a bioactive furofurandione-type fungal metabolite, has been achieved in a 21% overall yield from a commercially available ß,γ-unsaturated carboxylic acid via seven steps. The key steps of this synthesis include a highly diastereoselective Michael addition of a chiral oxazolidinone derivative to a nitro olefin, the exploitation of an aromatic ring as a masked carboxylic acid functionality, and the base-promoted elimination of nitrous acid to install the α-methylene lactone unit of sporothriolide in the final step.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alkenes
/
Furans
Language:
En
Journal:
J Org Chem
Year:
2021
Document type:
Article
Affiliation country:
Japan