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Total Synthesis of 1‐ O ‐Methyllateriflorone
Author(s) -
Nicolaou K. C.,
Sasmal Pradip K.,
Xu Hao,
Namoto Kenji,
Ritzén Andreas
Publication year - 2003
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.200351805
Subject(s) - moiety , claisen rearrangement , tandem , total synthesis , cascade , tetradecane , stereochemistry , key (lock) , chemistry , computer science , engineering , organic chemistry , operating system , chromatography , aerospace engineering
The unique spiroxalactone framework of lateriflorone ( 1 ) consists of a prenylated dihydrobenzoquinone moiety and a trioxatetracyclotetradecane system. A tandem Claisen rearrangement/Diels–Alder cascade was the key step in the synthesis of the complex tetradecane system, which was then used to prepare 1‐ O ‐methyllateriflorone ( 2 ).