Abstract
An enantioselective total synthesis of (+)-anthecularin, an antiplasmodial and antitrypanosomal sesquiterpene lactone, has been achieved in 3.9% overall yield through 18 steps from a known dibromo alcohol. The key features of the synthesis include an intramolecular Claisen-type cyclization of a formyl-protected hydroxyl lactone to construct a bicyclic intermediate with a quaternary stereogenic center and a stereocontrolled 1,2-addition of vinyllithium to a methoxyethyl-protected spirocyclic hydroxyl enone to install a tetrasubstituted asymmetric center with excellent diastereoselection. This first enantioselective synthesis of anthecularin enabled the determination of its absolute configuration as 2R, 3R, 4S, 8R.
Original language | English |
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Pages (from-to) | 3888-3891 |
Number of pages | 4 |
Journal | Organic letters |
Volume | 20 |
Issue number | 13 |
DOIs | |
Publication status | Published - 2018 Jul 6 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry