Hetero Diels–Alder Cycloaddition of Indene for the Formal Synthesis of Onychnine

Author: Hong Bor   Hallur Mahanandeesha   Liao Ju  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.36, Iss.11, 2006-06, pp. : 1521-1528

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Abstract

A highly regio- and stereoselective hetero Diels–Alder cycloaddition of indene with N-sulfonyl-1-aza-1,3-butadiene was achieved. Subsequent transformation of the 5 H -indeno [l,2- b ]pyridine via elimination and reduction provides a new route to azafluorenone (e.g., 1-methyl-4-azafluorene) for the synthesis of onychnine.