A Concise, Stereocontrolled Thiazolium Ylide Approach to Kainic Acid
β Scribed by Monn, James A.; Valli, Matthew J.
- Book ID
- 127204951
- Publisher
- American Chemical Society
- Year
- 1994
- Tongue
- English
- Weight
- 682 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0022-3263
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a βFull Textβ option. The original article is trackable v
Racemic nonactic acid was efficiently constructed in a convergent, stereocontrolled fashion (7 steps, 27%). The present synthesis features a stereocontrolled 1,3-dione reduction with NaBH 4 /Et 2 B(OMe) and an acid-promoted stereospecific cyclization in the formation of 7.
A formal synthesis of (-)-a-kainic acid was achieved from L-pyroglutamic acid. The C-4 substituent of the pyrrolidine ring was introduced by using a ketyl radical cyclization on an ene carbamate.