The preparation of α-tetralones from benzocyclobutenones via sequential thermal electrocyclic reactions

✍ Scribed by Derek N. Hickman; Timothy W. Wallace; J. Michael Wardleworth

• Book ID: 104214906
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 298 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)74896-9

✦ Synopsis

1-Alkenylbenzocyclobuten-1-ols, prepared from benzocyclobutenones I la the addition of alkenylmagnesmm brormdes, or the addmon of alkynylhthmm reagents followed by (E)-selective reduction of the trtple bond, undergo successtve thermal 4~ and 6~ electrocychc reactions leadmg to substituted 3,4-dthydro-l(ZH)-naphthalenones Substituted a-tetralones [3,4-dlhydro-1(2H)-naphthalenones] and their hnear fused homologues have various synthetic uses They are especially promment m the context of the anthracyclmes,t~2 featunng as intermediates3 and as targets, e g %demethoxyaranclamycmone 1,4 and the aureohc acid anhcancer agents,5 e g ohvomycln and chromomycm A3, which are based on the mcychc aglycones ohvm 2 and chromomycmone 3 respechvely 6