Re-erved in USl If, November 1972 ; recrived in ulc for publication 4 l!ecember 1972) Of the various possible synthetic approaches to sesquiterpenes of the hydroazulene varrety', solvolytic skeletal rearrangement of decalyl 2,3 and bicyclo-(4,3,l)decanyll tosylates has received the greatest amount
A new synthesis of a hydroazulenone
โ Scribed by P. Geetha; K. Narasimhan; S. Swaminathan
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 184 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
In recent years several approaches to hydroazulenes involving efficient and ingenious synthetic designs have been developed. 1 We report here a new route to 6-methyl-bicyclo(5,3,O)-deca-l,6-dien-3-one (4).2 Treatment of the bicyclic enedione (1) with dimethyloxosulfoniu methylide (DMSM)3 in dimet%l sulfoxide at 25.C followed by heating at 60.C gave a mixture of products.
๐ SIMILAR VOLUMES
In connection with periplanone A, acid-catalyzed reaction of germacrene-D epoxide has been carried out using A1C13 in ether to afford a hydroazulene which has been further transformed into one of the hydroazulenones proposed to be periplanone A. TWO sex pheromones of the American cockroach Periplane
exo-Methylene ketone 6 serves as a vehicle for elaboration of the C8 quaternary center en route to guanacastepene via a conjugate addition-alkylation sequence. Methylation of the cycloheptadienolate derived from 7 is highly selective for the desired relative stereochemistry, as determined by NMR and
Hypoglycin A, (III), a new aminoacid with marked hypoglycasmic properties was isolsted by Hassal' from unripe ackee fruit (Blighia sapida) and subsequently synthesised in six stages from 2-bromo-propene by Carbon, Martin and Svett2. In our three stage synthesis l-bromo--buta-2,3-diene3 was condensed