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A Concise Route to the Strongylophorines
Author(s) -
Yu Wanwan,
Hjerrild Per,
Overgaard Jacob,
Poulsen Thomas B.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602476
Subject(s) - semisynthesis , chemistry , combinatorial chemistry , stereochemistry , block (permutation group theory) , cascade , mathematics , geometry , chromatography
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 sp 3 C−H δ ‐lactonization are the key transformations that enable concise assembly of these bioactive polycyclic meroterpenoids.