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Formal Total Synthesis of (−)‐Apicularen A by a Strategy Based on Ring‐Closing Metathesis and Transannular Cyclization
Author(s) -
Jung YoungHee,
Kim YoungJu,
Lee Jieun,
Tae Jinsung
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700024
Subject(s) - ring closing metathesis , metathesis , tetrahydropyran , kinetic resolution , ring (chemistry) , total synthesis , formal synthesis , stereochemistry , chemistry , lactone , salt metathesis reaction , hydrolysis , combinatorial chemistry , resolution (logic) , sequence (biology) , organic chemistry , computer science , enantioselective synthesis , catalysis , programming language , biochemistry , polymerization , polymer
A formal synthesis of (−)‐apicularen A, a potent antitumor agent with unique biological properties, has been completed in a 15‐step sequence starting from a known, enantiomerically pure hydroxyepoxide, which was generated by using the Jacobsen hydrolytic‐kinetic‐resolution methodology. The 12‐membered macrocyclic lactone in the target was constructed by ring‐closing metathesis, and the trans ‐tetrahydropyran ring system was created through the transannular etherification of a hydroxyalkene.