Stereoselective Syntheses of trans-Anhydromevalonic Acid and trans-Anhydromevalonyl Group-Containing Natural Products.
J Nat Prod
; 85(4): 1052-1058, 2022 04 22.
Article
in En
| MEDLINE
| ID: mdl-35195424
ABSTRACT
Collective total syntheses of trans-anhydromevalonic acid (tAHMA) and trans-anhydromevalonyl (tAHM) group-containing natural products (pestalotiopin A, pestalotiopamide C, pestalotiopamide D, farinomalein E, eleutherazine B, and trichocyclodipeptide A) were achieved using tAHMA esters as key intermediates. To this end, tAHMA tert-butyl ester was newly prepared by Z-vinyltosylation of tert-butyl 3-oxo-5-((triisopropylsilyl)oxy)pentanoate followed by the Negishi cross-coupling reaction with Me2Zn. tAHMA esters were converted to the target natural products via esterification or amidation. Comparison of the spectroscopic data of synthetic and natural products confirmed the E-configuration of the tAHM moieties in the natural products.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Biological Products
Language:
En
Journal:
J Nat Prod
Year:
2022
Document type:
Article
Affiliation country:
Japan