Bioinspired Synthesis of Microstegiol and Biosynthetically Related Skeleton-Rearranged Abietanes
Ling Huang, Peng Wang, Fan Xia, Lu Chen, Wengui Wang, Gang Xu, Jun Deng
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.
Topics & Concepts
ChemistrySkeleton (computer programming)StereochemistryCombinatorial chemistryAnatomyMedicineBiological Activity of Diterpenoids and BiflavonoidsMicrobial Natural Products and BiosynthesisBioactive Natural Diterpenoids Research