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2005
Terpenes
U 0200
32- 170
Sulfanyl Radical-Induced Cyclization of Linalyl Acetate to the Iridane Skeleton:
A Short Synthesis of (±)-Dehydroiridomyrmecin. — The total synthesis of dehydroiridomyrmecin (XII) involves a 5-exo-trig cyclization promoted by the addition of sulfanyl radicals to the mono-substituted double bond of linalyl acetate derivative (V) as
a key step. The C-7-centered radical, generated by Markovnikov addition, intramolecularly adds to the ∆2 double bond yielding the cyclopentane intermediate (VII). Regioselective deacetylation of (VII), followed by straightforward functional group transformations and subsequent chemoselective saponification of the trifluoroacetate group of
(XI) furnish the natural compound (XII). — (BARRERO*, A. F.; ARSENIYADIS, S.;
HERRADOR, M. M.; QUILEZ DEL MORAL, J. F.; ARTEAGA, J. F.; SANCHEZ, E.
M.; Synlett 2005, 4, 591-594; Dep. Quim. Org., Fac. Farm., Univ. Granada, E-18071
Granada, Spain; Eng.) — H. Hoennerscheid
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