Abstract
The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal alkenes by the combined use of OsO4 and PhB(OH)2; and (iv) β(1,2-cis)-selective glycosidation via a 1,3-anchimeric assistance from a 4-methoxybenzoyl group.
Original language | English |
---|---|
Pages (from-to) | 6931-6937 |
Number of pages | 7 |
Journal | Journal of the American Chemical Society |
Volume | 128 |
Issue number | 21 |
DOIs | |
Publication status | Published - May 31 2006 |
Externally published | Yes |
ASJC Scopus Subject Areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry