A practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of the A practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of thA practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of the adduct. The synthesis gives a 17% overall yield from nitrone 2.
A Concise Total Synthesis of (+)-Heliotridine / F. M. Cordero; F. Pisaneschi; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2003:(2003), pp. 4373-4375. [10.1002/ejoc.200300405]
A Concise Total Synthesis of (+)-Heliotridine
CORDERO, FRANCA MARIA;BRANDI, ALBERTO;
2003
Abstract
A practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of the A practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of thA practical synthesis of the necine base (+)-heliotridine (1) is reported here. The present total synthesis is based on the highly selective 1,3-dipolar cycloaddition of (S)-3-tert-butoxypyrroline N-oxide (2) to the commercially available ethyl 4-bromocrotonate, followed by a suitable elaboration of the adduct. The synthesis gives a 17% overall yield from nitrone 2.
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