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Total Synthesis of Ceratopicanol through Tandem Cycloaddition Reaction of a Linear Substrate
Author(s) -
Lee SangShin,
Kim WonYeob,
Lee HeeYoon
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200497
Subject(s) - trimethylenemethane , cycloaddition , tandem , diazo , substrate (aquarium) , chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , catalysis , biology , ecology , composite material
Total synthesis of ceratopicanol ( 1 ) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary carbon centers and showed an unusual diastereoselectivity.