Synthesis of indolizidine alkaloids via the intramolecular imino Diels-Alder reaction

…, HF Schmitthenner, J Shringarpure…

Index: Khatri, Nazir A.; Schmitthenner, Hans F.; Shringarpure, Jayant; Weinreb, Steven M. Journal of the American Chemical Society, 1981 , vol. 103, # 21 p. 6387 - 6393

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Citation Number: 75

Abstract

Abstract: An intramolecular imino Diels-Alder strategy has been developed for total synthesis of the indolizidine alkaloids 6-coniceine (l), tylophorine (2), elaeokanine A (3), and elaeokanine B (4). In all cases, an acyl imine dienophile was generated thermally in situ from a methylol acetate precursor. Diene-methyl01 acetate 8 has been cyclized via 10 to lactam 11, which was converted to 6-coniceine. Similarly, intermediate methylol acetate ...