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A direct synthesis of trans 2-arylbenzocyclobutenol, a potential intermediate for podophyllotoxin synthesis: Use of lda for benzyne formation and trapping

✍ Scribed by Michael E Jung; Gregory T Lowen

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
216 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of a-alkoxyaryl bromides with LDA in THF produces the corresponding aryne which can be trapped intramolecularly by an anion u to a nitrile to produce a substituted benzocyclobutenyl nitrile, the precursor of a trans arylbenzocyclobutenol potentially useful for podophyllotoxin synthesis.

Recently we published an account of our work2 on a proposed synthesis of the active principle of podophyllin, podophyllotoxin 1, derivatives of which have shown great promise as cancer chemotherapeutic agents, such as Etoposide and Teniposide.3 Our proposed approach to 1 involved an intramolecular Diels-Alder cycloaddition of

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