Enantiomeric β-angelica lactone epoxides: their syntheses from suitable chiral precursors and their use in the preparation of blastmycinone
✍ Scribed by Rosa M. Ortuño; Daniel Alonso; Jaume Cardellach; Josep Font
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 711 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Sumnary.-Synt+see.of (S)+angelica lactone from &-tartaric acid and (RI-yhydroxymethyl-y-butyrolactone, 5, are reported. Alternative routes to prepare 5 from s-and R-glutamic acids and D-ribonolactone. respectively, am also presented. Epoxides deriwd from (RI-and 7s)-R+ngelica la&ones have been obtained and their uae in the synthesis of both (+)-and (-l-blastmycinone, 24, has been established.
Ir4TMDWTION
The use of simple natural products ss chiral precursors in the synthesis of optically active compounds haa been widely applied in the last ten years.' In this way, following our studies on the preparation of interesting Y-lactonic substances, 2 we have investigated synthetic routes to accede to both enanticmers (-j-(E)-and (+)-(S)-Bangelica lactones, t-j-1 and (+)-1 respectively, and to some derivatives that could be employed as useful precursors In enantioselective synthesis.