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Total Synthesis of (+)‐ trans ‐Dihydronarciclasine by a Catalytic Enantioselective Regiodivergent Nitroso Diels–Alder Reaction
Author(s) -
Jana Chandan Kumar,
Studer Armido
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800903
Subject(s) - enantioselective synthesis , yield (engineering) , diels–alder reaction , nitroso , catalysis , chemistry , alder , stereochemistry , organic chemistry , biology , materials science , botany , metallurgy
A novel approach to enantiomerically pure (+)‐ trans ‐dihydronarciclasine ( 1 ), a biologically active natural product of the Amaryllidaceae group, uses a catalytic enantioselective regiodivergent nitroso Diels–Alder reaction as the key step. Compound 1 is prepared in a 17‐step synthesis in 5.6 % overall yield.