𝔖 Bobbio Scriptorium
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Photo-oxidation of some benzylisoquinoline-derived alkaloids

✍ Scribed by I.R.C. Bick; J.B. Bremner; P. Wiriyachitra

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
137 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis

We wish to report a photo-oxidative cleavage reaction of some benzylisoquinoline-based alkaloids, which should be particularly useful in structural studies of bisbenzylisoquinolines not readily amenable to the usual degradative methods.

Ultraviolet irradiation' of laudanosine (I) in the presence of oxygen gave (11)(45X), veratraldehyde (IV)(67%), and the carbinolamine (III), isolated as its chloride salt 2 or as its reduction (NaBH4) product (V)(42%). The same products were obtained using methylene blue as sensitiser (45 mins; uranyl oxalate filter sleeve), but in lower yield: (II), 32%; (IV), 39%; (V), 15%.

No noticeable oxidation of laudanosine occurred in the dark.

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