Abstract
The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.
Original language | English (US) |
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Pages (from-to) | 9169-9202 |
Number of pages | 34 |
Journal | Tetrahedron |
Volume | 53 |
Issue number | 27 |
DOIs | |
State | Published - Jul 7 1997 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry