Abstract
The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.
Original language | English |
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Pages (from-to) | 4581-4587 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 68 |
Issue number | 24 |
DOIs | |
Publication status | Published - 2012 Jun 17 |
Keywords
- Cyclobutane
- Cytotoxic
- Epoxy nitrile
- Rumphellaone
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry