Stereoselective Syntheses of (+)-Rhopaloic Acid A and (-)-ent-and (±)-rac-Rhopaloic Acid A. -Total syntheses of natural rhopaloic acid (XIII), its enantiomer and racemate via successive homologation of farnesol (I) and cyclization to form the tetrahydropyran ring are described. The asymmetric synthe
Stereoselective syntheses of (+)-rhopaloic acid A and (−)-ent- and (±)-rac-rhopaloic acid A
✍ Scribed by Takagi, Ryukichi; Sasaoka, Asami; Nishitani, Hiroko; Kojima, Satoshi; Hiraga, Yoshikazu; Ohkata, Katsuo
- Book ID
- 120045000
- Publisher
- Royal Society of Chemistry
- Year
- 1998
- Weight
- 172 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1472-7781
- DOI
- 10.1039/A707204J
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📜 SIMILAR VOLUMES
A six-step synthesis of rhopaloic acid A (1E) was accomplished in 25% overall yield using the Pd(II)mediated cyclization and methoxycarbonylation of allenyl alcohol 3, which affords 83% of a 6:1 mixture of tetrahydropyranylacrylates 2 and 8, as the key step.
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Asymmetric Synthesis of Rhopaloic Acid A Analogues and Their Biological Properties. -In order to study structure-activity relationships of cytotoxic rhopaloic acid, related analogues such as (X) are synthesized. The routes are based on asymmetric alkylation of a chiral oxazolidine (I) and construct