Abstract
The first total synthesis of two herbicidal natural products bacilosarcins A and B, the former of which incorporates a totally unprecedented heterobicyclic ring system and the latter contains a very rare heterecyclic structural motif, has been accomplished. The irregular ring systems in bacilosarcins A and B were constructed in very simple manners by means of an Amadori-type /V-alkylation reaction as well as by taking advantage of the thermodynamic stability of the targeted rings. The total synthesis of PM-94128 and Y-05460 M-A, cytotoxic natural products of microbial origin, has also been accomplished by a concise nine-step sequence from L-leucine and L-valine, respectively. The first synthesis of Y-05460 M-A enabled its stereochemical determination.
| Original language | English |
|---|---|
| Pages (from-to) | 387-398 |
| Number of pages | 12 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 68 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2010 Apr 1 |
Keywords
- Amadori rearrangement
- Amicoumacin
- Bacilosarcin
- Epoxide ring opening
- Heterocycles
- Hydro-xylactonization
- Isocoumarin
- Stereoconvergent cyclization
- Tautomerization
ASJC Scopus subject areas
- Organic Chemistry