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Org Lett. 2003 Sep 4;5(18):3205-8.

A concise total synthesis of (+/-)-alantrypinone by a novel hetero-Diels-Alder reaction.

Author information

1
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. kende@chem.rochester.edu

Abstract

[reaction: see text] An efficient total synthesis of (+/-)-alantrypinone (1) and its 17-epi isomer (17) has been accomplished employing a novel aza-Diels-Alder reaction as the key step. The reaction sequence comprises 8 steps starting from anthranilic acid and proceeds in 13.5% overall yield. An interesting anionic equilibration between 1 and its epimer 17 has also been discovered.

PMID:
12943388
DOI:
10.1021/ol030070l

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