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Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.
| Publication Type | Journal Article |
| Authors | Ng, PY, Masse CE, and Shaw JT |
| Abstract | Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps. |
| Year of Publication | 2006 |
| Journal | Organic letters |
| Volume | 8 |
| Issue | 18 |
| Pages | 3999-4002 |
| Date Published (YYYY/MM/DD) | 2006/08/31 |
| ISSN Number | 1523-7060 |
| DOI | 10.1021/ol061473z |
| PubMed | http://www.ncbi.nlm.nih.gov/pubmed/16928058?dopt=Abstract |
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