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An Efficient Substrate‐Controlled Approach Towards Hypoestoxide, a Member of a Family of Diterpenoid Natural Products with an Inside‐Out [9.3.1]Bicyclic Core
Author(s) -
McGrath Nicholas A.,
Lee Christopher A.,
Araki Hiroshi,
Brichacek Matthew,
Njardarson Jon T.
Publication year - 2008
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.200804237
Subject(s) - bicyclic molecule , metathesis , product (mathematics) , natural product , ring closing metathesis , substrate (aquarium) , closing (real estate) , salt metathesis reaction , computer science , natural (archaeology) , combinatorial chemistry , chemistry , stereochemistry , organic chemistry , biology , polymerization , mathematics , law , political science , ecology , paleontology , geometry , polymer
The bicycle works : A versatile route to the verticillane family of natural products has been devised, utilizing a strategically rigidified relay ring‐closing metathesis reaction. The shape of the bicyclic product was used to stereoselectively control the bisepoxidation reaction towards hypoestoxide, a member of this natural product family.