Acyclic stereoselection via cyclic hydroboration. Synthesis of the Prelog-Djerassi lactonic acid.
β Scribed by W.Clark Still; Kenneth R. Shaw
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 199 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
## Cyclic hydroboration of an appropriately substituted 1.5~diene yields a 1,5 dial as the major product which can be converted to the racemic Prelog-Djerassi lactone. The widespread occurrence of the three carbon unit 1 in natural products of current synthetic interest has prompted us to investig
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 --