Diastereoselective radical cyclization reactions; the synthesis of O -methylcorytenchirine
Highly diastereoselective cyclization of radicals such as 4 provides a model for the synthesis of 8-substituted berbines. Thus the reaction of 6,7-dimethoxyisoquinoline 21 with the acid chloride 19 affords the key intermediate 22, which undergoes free radical cyclization on treatment with tributylstannane to give (±)-23 as the sole product. Reduction of 23 affords (±)-O-methylcorytenchirine 14. The carbamate 24 does not undergo radical cyclization when treated with tributylstannane, but the...[Show more]
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