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Enantioselective Total Synthesis of (+)‐Ophiobolin A
Author(s) -
Tsuna Kazuhiro,
Noguchi Naoyoshi,
Nakada Masahisa
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204119
Subject(s) - enantioselective synthesis , total synthesis , ring (chemistry) , intramolecular force , stereochemistry , metathesis , stereoselectivity , chemistry , ring closing metathesis , salt metathesis reaction , substrate (aquarium) , catalysis , organic chemistry , polymerization , biology , ecology , polymer
The enantioselective total synthesis of (+)‐ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)‐ophiobolin A through a stereoselective intramolecular Hosomi–Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight‐membered carbocyclic ring through ring‐closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.