A Short Enantioselective Total Synthesis of the Fundamental Pentacyclic Triterpene Lupeol
- 9 September 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (39), 13928-13929
- https://doi.org/10.1021/ja906335u
Abstract
The first enantioselective synthesis of lupeol has been developed by applying two carefully crafted cation-π cyclization stages to generate the pentacyclic structure with complete stereocontrol. The synthesis (Scheme 1) is noteworthy because of its brevity and also because it solves a longstanding problem in the field of natural product synthesis.Keywords
This publication has 11 references indexed in Scilit:
- TriterpenoidsNatural Product Reports, 2008
- Rapid and Enantioselective Synthetic Approaches to Germanicol and Other Pentacyclic TriterpenesJournal of the American Chemical Society, 2008
- On the origins of triterpenoid skeletal diversityPhytochemistry, 2004
- A Mechanistically Guided Design Leads to the Synthesis of an Efficient and Practical New Reagent for the Highly Enantioselective, Catalytic Dihydroxylation of OlefinsOrganic Letters, 2003
- Highly Effective Transition Structure Designed Catalyst for the Enantio- and Position-Selective Dihydroxylation of PolyisoprenoidsOrganic Letters, 2001
- A mechanistically designed bis-cinchona alkaloid ligand allows position- and enantioselective dihydroxylation of farnesol and other oligoprenyl derivatives at the terminal isopropylidene unitTetrahedron Letters, 1995
- A short and convergent enantioselective synthesis of (3S)-2,3-oxidosqualeneTetrahedron Letters, 1993
- Total synthesis of lupeolJournal of the American Chemical Society, 1971
- Isolation of Lupeol from the Osage Orange (Maclura pomifera Raf.)1Journal of the American Chemical Society, 1942
- Zur Kenntnis der Triterpene. (54. Mitteilung). Über Lupenal und Lupenalol, sowie deren weitere UmwandlungenHelvetica Chimica Acta, 1940