Stereoselective reactions of chiral enolates. Application to the synthesis of (+)-prelog-djerassi lactonic acid.
β Scribed by D.A. Evans; J. Bartroli
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 241 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
The cycloheptenone (lc), a precursor to the (2) Prelog -Djerassi lactonic acid (2), has been synthesized stereoselectively from cyclohepta-1,3-diene.
The (+)-Prelog-Djetassi lactone methyl ester 1 was obtained from tmns-pulegenic acid 2 in seven steps jn 22 % overall YjeJd; three more steps from an unwanted dkstereoisomergave additionnal5 %. Resume : L 'ester methylique de la Iactone de Prelog-Djemssi I a et6 obtenu en sept &apes i partir de I 'a
The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from Npropionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 ---) 7) followed by saponification of the sultam moiety (7 --