A Concise Route to the Strongylophorines

An efficient eight‐step semisynthesis of strongylophorine‐2 from the abundant building block isocupressic acid is reported. The route represents the first synthetic entry into this class of natural products and provides access to six additional family members. A novel iron(III)‐mediated rearrangemen...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-07, Vol.55 (29), p.8294-8298
Main Authors: Yu, Wanwan, Hjerrild, Per, Overgaard, Jacob, Poulsen, Thomas B.
Format: Article
Language:English
Subjects:
Assembly
Biocompatibility
Biomedical materials
cascade reactions
cyclization
C−H activation
Iron
Natural products
Semisynthesis
Surgical implants
Transformations
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Summary:An efficient eight‐step semisynthesis of strongylophorine‐2 from the abundant building block isocupressic acid is reported. The route represents the first synthetic entry into this class of natural products and provides access to six additional family members. A novel iron(III)‐mediated rearrangement–cyclization cascade and a directed photochemical sp3 C−H δ‐lactonization are the key transformations that enable concise assembly of these bioactive polycyclic meroterpenoids. No detours: A powerful semisynthetic strategy to meroterpenoids of the strongylophorine (STR) family is reported. Starting from the abundant sesquiterpene isocupressic acid, a new Lewis acid mediated allylic rearrangement–cyclization cascade and a strategic methyl C−H activation reaction enabled expedient construction of seven members of the STR family, including STR‐2.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201602476