Synthesis of the Prelog–Djerassi Lactone via an Asymmetric Hydroformylation/Crotylation Tandem Sequence
✍ Scribed by Risi, Roberto M.; Burke, Steven D.
- Book ID
- 120545639
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 463 KB
- Volume
- 14
- Category
- Article
- ISSN
- 1523-7060
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📜 SIMILAR VOLUMES
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
## 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 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 --