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Collective Synthesis of Natural Products Sharing the Dihydro‐γ‐Ionone Core
Author(s) -
Castillo Alexis,
Silva Lucia,
Briones David,
Quílez del Moral José F.,
Barrero Alejandro F.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500208
Subject(s) - chemistry , enantioselective synthesis , total synthesis , stereochemistry , bicyclic molecule , derivative (finance) , ionone , molecule , squalene , formal synthesis , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics
We decided to follow the so‐called “collective total synthesis” approach to synthesize several structurally different molecules from a common intermediate possessing appropriate stereochemistry and functionalities. As the common precursor for the efficient preparation of these bioactive molecules, we chose (+)‐3,4‐dihydro‐γ‐ionone ( 1 ), a natural compound present in minor quantities in ambergris and in the plant Bellardia trixago . Thus, we report herein the enantioselective synthesis of siccanochromene F ( 2 ), metachromins U ( 3 ) and V ( 4 ), and bicyclic squalene derivative 5 as well as the formal syntheses of ambrein ( 6 ), phenazinomycin ( 7 ), and (–)‐siccanin ( 8 ).
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