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A Formal Total Synthesis of Salvadione
Author(s) -
Maier Martin E.,
Bayer Alexander
Publication year - 2006
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.200600361
Subject(s) - chemistry , iodide , alkylation , bromide , intramolecular force , total synthesis , tricyclic , friedel–crafts reaction , aryl , yield (engineering) , lithium iodide , stereochemistry , alkyl , organic chemistry , medicinal chemistry , catalysis , materials science , electrode , electrolyte , metallurgy
Abstract The tricyclic 6‐7‐6 core structure of the triterpene salvadione ( 1 ) was obtained in an efficient manner from the aryl bromide 16 and the alkyl iodide 35 carrying a methylenecyclohexane group at the terminus. Alkylation of the anion derived from 16 with the iodide 35 gave the tethered system 36 . This compound was converted into the allylic bromide 40 . Finally, a Lewis acid mediated intramolecular Friedel–Crafts alkylation furnished the target structure 13 in good overall yield. The synthesis of tricyclic compound 13 represents a formal total synthesis of salvadione ( 1 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)