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A Convergent Synthesis of (±)‐α‐ and β‐Himachalenes
Author(s) -
Oppolzer Wolfgang,
Snowden Roger L.
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640815
Subject(s) - chemistry , hydrogenolysis , intramolecular force , regioselectivity , convergent synthesis , stereochemistry , organic chemistry , catalysis
(±)‐α and β‐Himachalene, 5 and 6 , have been synthesized in a convergent manner from 3,3‐dimethylacrolein ( 9 ), the ester enolate 10 and the silyloxypentadienyllithium 7 . The key steps are the regioselective γ‐addition of the dienal 13 to 7 and the intramolecular Diels‐Alder addition 15 → 16 . Hydrogenolysis of the diethylphosphate group and functionalization at C (5) completed the synthesis of 5 and 6 .