- Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine
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Functionalized bicyclo[3.2.1]octanes, -oxabicyclo-[4.3.0]nonanes, 3-azabicyclo[3.3.0]octanes, and 3-azabicyclo[4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo[4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. α-Skytanthine, a typical 3-azabicyclo[4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol.
- Takeda, Kazutaka,Toyota, Masahiro
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p. 9909 - 9921
(2012/02/06)
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- CYCLOPENTANOMONOTERPENE ENOL ACETATES FROM NEPETA LEUCOPHYLLA
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Three new iridodial derivatives, >-2--5-methylcyclopentanecarboxaldehyde (iridodial β-monoenol acetate), >-2--5-methylcyclopentyl>methyl acetate (dihydroiridodial diacetate), or their enantiomers, and -2-3-methylcyclopentyl>-1-propenyl acetate (iridodial dienol diacetate) of unknown configuration have beren isolated from the essential oil of Nepeta leucophylla gathered in the Kumaun Region of India. Key Word Index - Nepeta leucophylla; Labiatae; cyclopentanomonoterpenes; ir idoids, iridodial enol acetates.
- Bottini, Albert T.,Dev, Vasu,Shah, G. C.,Mathela, C. S.,Melkani, A. B.,et al.
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p. 1653 - 1658
(2007/10/02)
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- ENANTIOSELECTIVE SYNTHESES OF (+)-α-SKYTANTHINE, (+)-δ-SKYTANTHINE AND (+)-IRIDOMYRMECIN BY AN INTRAMOLECULAR MAGNESIUM-ENE REACTION.
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Starting from (S)-3-methyl-1-penten-5-ol 3a enantiomerically pure (+)-α-skytanthine 9, (+)-δ-skytanthine 11 and (+)-iridomyrmecin 12 were synthesized via the magnesium-ene rection 2*1.
- Oppolzer, Wolfgang,Jacobsen, E. Jon
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p. 1141 - 1144
(2007/10/02)
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- Pd(0) PROMOTED REARRANGEMENT OF 2-(1,3-BUTADIENYL)CYCLOPROPANE-1,1-DICARBOXYLATE ESTERS TO 2-ALKENYL-3-CYCLOPENTENE-1,1-DICARBOXYLATE ESTERS
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The title dienylcyclopropanes smoothly rearrange to five-membered rings in the presence of Pd(0) catalyst under mild conditions.
- Morizawa, Yoshitomi,Oshima, Koichiro,Nozaki, Hitosi
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p. 2871 - 2874
(2007/10/02)
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