Bioinspired Synthesis of Microstegiol and Biosynthetically Related Skeleton-Rearranged Abietanes
Ling Huang1, Peng Wang2, Fan Xia3
1School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan 250022, People's Republic of China.
Abstract:
We report a bioinspired synthesis of microstegiol and biosynthetically related skeleton-rearranged abietane diterpenoids from commercially available carnosic acid. The strategy features a Wagner-Meerwein type methyl migration followed by several cascade transformations, enabling the divergent synthesis of five abietane diterpenoids, including viridoquinone, prattinin A, saprorthoquinone, microstegiol, and 1-deoxyviroxocin.
More Related Videos
Related Concept Videos
Synthetic Biology
Golden rice
Golden rice is a genetically modified...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


