Abstract
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.
Original language | English |
---|---|
Pages (from-to) | 5476-5486 |
Number of pages | 11 |
Journal | Chemistry - A European Journal |
Volume | 19 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2013 Apr 22 |
Keywords
- cyclization
- natural products
- ophiobolin A
- spiro compounds
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry