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An alternative synthesis of the indole alkaloid vinoxine

✍ Scribed by M.-Lluïsa Bennasar; Ester Zulaica; Juan-Miguel Jiménez; Joan Bosch

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
243 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

An alternative synthesis of (f)-vinoxine, based on the nucleophilic addition of an ester a-anion to a 3-acetylpyridinium salt, acid-induced cyclization of the resultant 1.4-dihydropyridine, and stereoselective elaboration of the @)-ethylidene substituent, is reported. Vinoxine' is a minor indole alkaloid isolated' from Vinca minor L., which possesses the tetracyclic 2,6-methano[l,4ldiazocino[l,Z-glindole system characteristic of C-mavacurine alkaloids 3 but whichdiffers from those inasmuch as the C-6/C-74 bond, connecting the indole 3-position and the tryptamine two-carbon chain, is broken. We have previously reported the first total synthesis 5,6 of (+)-vinoxine (8b) and its unnatural epimer [ (+I-16-epivinoxine, 8a 1 as well as the reassignment of the relative configuration at C-16 of this alkaloid. 5,7 The synthesis involved the addition of a stabi-

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