Journal
CHEM
Volume 5, Issue 6, Pages 1671-1681Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2019.04.023
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Funding
- NNSFC [21625201, 21661140001, 91853202, 21521003, 81630093]
- National Key Research and Development Program of China [2017YFA0505200]
- National High Technology Project 973 [2015CB856200]
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Herein, we describe the protecting-group-free total synthesis of two structurally diverse Isodon diterpenoids, (+)-ent-kauradienone (3) and(-)-jungermannenone C (4), in 12 and 14 steps respectively, through sequential applications of three radical-based reactions, including the photoinduced skeletal rearrangements of bicyclo[ 3.2.1] octene ring systems. Further investigations of this photochemical radical rearrangement on a series of diverse terpenoids demonstrated both the unparalleled functional-group tolerance and the broad applicability of such late-stage photochemical rearrangements for the synthesis of structurally diverse and complex small molecules. Overall, the mild nature of late-stage photoinduced skeletal rearrangements might suggest that they are possible in a biological setting in unappreciated complimentary biosynthetic pathways.
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