z-logo
Premium
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 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom