A concise total synthesis of (+/-)-alantrypinone by a novel hetero-Diels-Alder reaction.
[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.
Kende
Andrew S
AS
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. kende@chem.rochester.edu
Fan
Junfa
J
Chen
Zecheng
Z