A new synthetic approach is described for building the coumarin scaffold through the Lewis acidpromoted cyclization of novel aryl 3-(dimethylamino)prop-2-enoates 2a -2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a -4f with the Bredereck reagent. T
✦ LIBER ✦
Natural product chemistry, 139. Synthesis of the natural coumarins (E)-suberenol, cyclobisuberodiene and two other related new coumarins
✍ Scribed by Reisch, Johannes ;Herath, H. M. T. Bandara ;Kumar, N. Savitri
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 271 KB
- Volume
- 1990
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The total synthesis of (E)‐Suberenol (1) was carried out under the conditions of palladium‐catalysed Heck condensation. Two other new coumarins, (E)‐7‐methoxy‐6‐(3‐methyl‐1,3‐butadienyl)coumarin [(E)‐suberodiene] (3) and (E)‐7‐methoxy‐6‐(3‐methyl‐1‐butenyl)coumarin [(E)‐suberenene] (4) and cyclobisuberodiene (2) were synthesised from (E)‐suberenol.
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