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A direct synthesis of hydroazulenones

✍ Scribed by P.T. Lansbury; P.M. Wovkulich; P.E. Gallagher

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 101 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95578-9

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✦ Synopsis

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 of attention for preparing bulnesol and its guaiazulenic relatives.

Although quite lengthy, these routes have allowed for partial 193 or total2 stereochemical control in elaborating the asymmetric centers in the precursors and hence also in the rearranged product.

We now wish to report an extremely rapid construction of hydroazulenones wherein chloro olefin annelation 4 permits direct entry into the bicyclo(5,3,0)decane ring system and, in addition, to a variety of 4-and/or 5-substituted azulenes.

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