Synthetic applications of 2-aryl-4-piperidones. V1.: Synthesis of the fundamental tetracyclic skeleton of ervitsine and its 20-deethylidene-6,16-dihydro analogue☆
The synthesis of the basic tetracyclic skeleton 2 of ervitsine and its 20-deethylidene-6,16-dihydro analogue 4 is reported.
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Cited by (9)
Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: Access to the tetracyclic ring system of ervitsine
2012, TetrahedronCitation Excerpt :Despite the variety of strategies used, all routes have in common the formation of the central carbocyclic ring in the last synthetic steps, either by cyclization of an iminium-type ion upon the indole 3-position (bond formed C5–C7, a)3a,d,4,5 or by Friedel–Crafts acylation of the indole 2-position (bond formed C2–C3, b).3b,c,e Our long-standing interest in the development of indole annulation methodologies led us to envisage a straightforward synthetic approach to the bridged ervitsine framework relying on an indole-templated ring-closing metathesis (RCM)6 to first construct the central seven-membered ring and a vinyl halide Heck cyclization7 to close the piperidine ring and at the same time install the requisite 20E-ethylidene substituent (bond formed C15–C20, c).8 As shown in Scheme 1, the metathetic ring closure of 2,3-dialkenylindoles of general structure A would provide cyclohepta[b]indoles B, with the appropriate double bond functionality for the subsequent intramolecular Heck reaction with the amino-tethered vinyl halide.9
A straightforward entry to the ervitsine skeleton. Synthesis of 16-demethyleneervitsine
1992, Tetrahedron LettersBiomimetic total synthesis of ervitsine and indole alkaloids of the ervatamine group via 1,4-dihydropyridines
1997, Journal of Organic ChemistryA unified strategy for the synthesis of bridged indole alkaloids and their close analogues
2013, Targets in Heterocyclic SystemsAn efficient and novel approach for the synthesis of substituted N-aryl lactams
2012, Organic and Biomolecular Chemistry
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For the previous paper in this series, see: Diez, A.; Tona, M.; Rubiralta, M., Tetrahedron, 1990, 46, 4393.