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An interesting application of photocyclisation in aporhoeadane alkaloid synthesis

✍ Scribed by S.V. Kessar; Tejvir Singh; Rahul Vohra

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
195 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of 2-carboethoxybenzoyl chloride with 3,4_dihydro-6,7-dimethoxyisoquinoline afforded a ring open aldehydic phthalimide(3) which on thioacetal formation and photocyclisation followed by deketalisation gave 8,14-dioxo-13-hydroxyaporhoeadane (6). Chilenine (8b) is an alkaloid having a string of contiguous functionalities appended on to an aporhoeadane skeleton. 1 We report that this structural pattern can very simply be put together through photocyclisation of a thioacetal imide 2 (4).

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