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Synthesis and nmr data of the strychnos indole alkaloid tubifoline

✍ Scribed by Mercedes Amat; Ana Linares; Javier Muñoz; Joan Bosch

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
239 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total synthesis of3 the %z&no~ indole alkaloid tubifoline and detailed H-and C-NMR data of thisalkaloid are reported.

Tubifoline is a pentacyclic

Stigchao~ indole alkaloid, 1 having the Strychnan skel-eta1 type, whose isolation and structural elucidation were reported by Schmid in 1964. 2 Its most characteristic structural features are the presence of an indolenine unit and the absence of the C-173 atom that is present in the greater part of S.tnychnon alkaloids. In 1968 Harley-Mason reported4 the first total synthesis of (+I-tubifoline according to a strategy that involves, as the final, key step, the simultaneous formation of C and E rings (C3-C7 bond formed1 by transannular oxidative cyclization of a stemmadenine-type system. Although two formal 5 and a total 6 syntheses of (+)-tubifoline have been reported since that time, all of them converge to intermediates used by Harley-Mason. Ref 7 (f)-TUBIFOLIDINE (+)-TUBIFOLINE Reagents and conditions: (i) NaH, ClC02Me, DME, 600; (ii) Raney-Ni, EtOH, 780 I 90 min; (iii) 1N NaOMelMeOH, 650, 60 min.

6373

Recently we achieved the total synthesis of (+I-tubifolidine,

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