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Sequential Annulation in Molecular Construction. A Short, Stereocontrolled Synthesis of (±)‐Hirsutene
Author(s) -
Paquette Leo A.,
Moriarty Kevin J.,
Shen ChienChang
Publication year - 1991
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199100022
Subject(s) - chemistry , annulation , yield (engineering) , key (lock) , ethylene , scheme (mathematics) , total synthesis , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy , ecology , biology
Abstract A total synthesis of (±)‐hirsutene has been achieved in 9 steps and in 14% overall yield via a twofold cycloadditive scheme that utilizes 4,4‐dimethylcyclopentene, 1‐(trimethylsilyloxy)butadiene, and ethylene as the three key building blocks.