Pheromones, 65. Identification of the volatile components of the mandibular gland secretion of the ant <i>Manica rubida</i>: Structure elucidation, synthesis, and absolute configuration of Manicone

Bestmann, Hans Jürgen; Attygalle, Athula B.; Glasbrenner, Jürgen; Riemer, Roland; Vostrowsky, O.; Constantino, Maurício Gomes; Меликян, Г. С.; Morgan, E. David

doi:10.1002/jlac.198819880111

Cited by 25 publications

(2 citation statements)

References 17 publications

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“…The majority of the enones 14c,f − j were prepared by allowing glycoaldehyde to react with the appropriate stabilized keto ylide in refluxing CHCl 3 , Scheme and Table . 6d, Both the alkyl-substituted enones 14g and 14h could not be readily separated from TPPO by chromatography and so were used without rigorous purification. Finally, treatment of 1,2-dioxine 2a with Co(II) Salen and then exposure to triphenylphosphine gave 14a according to a published literature procedure 6a…”

Section: Resultsmentioning

confidence: 99%

A Novel Synthesis of Functionalized Tetrahydrofurans by an Oxa-Michael/Michael Cyclization of γ-Hydroxyenones

et al. 2003

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An approach to highly functionalized tetrahydrofuran derivatives based upon a novel Oxa-Michael/Michael dimerization of cis-gamma-hydroxyenones is presented. The reaction begins with either 1,2-dioxines or trans-gamma-hydroxyenones and proceeds by addition of one molecule of trans-gamma-hydroxyenone to another molecule of cis- or trans-gamma-hydroxyenone catalyzed by an alkoxide or hydroxide base. Subsequent intramolecular Michael addition of the keto-enolate gives the observed tetrahydrofurans. Substitution at both the 2- and 4-positions of the gamma-hydroxyenone is tolerated; however, for 4-substituted gamma-hydroxyenones, selectivity issues arise due to the possibility of heterochiral or homochiral dimerizations. The major products were those with all contiguous groups trans.

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Section: Resultsmentioning

confidence: 99%

A Novel Synthesis of Functionalized Tetrahydrofurans by an Oxa-Michael/Michael Cyclization of γ-Hydroxyenones

et al. 2003

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“…Another doubly branched ketone, 4,6-dimethyl-4-octen-3-one (''manicone''), was identified as an alarm pheromone from Manica ants, [17] and was found to have a (4E,6S)-configuration. [18] As for the biosynthesis of the compounds identified here, methyl branching in the ketones is presumably introduced by replacement of an acetate (malonate) by a propanoate (or methylmalonate) unit along a polyketide route. This is depicted in Scheme 3, where [X], [Y], and [Z] are activators.…”

Section: Scheme 2 Enantioselective Synthesis Of 4cmentioning

confidence: 99%

Identification and Assignment of the Absolute Configuration of Biologically Active Methyl-Branched Ketones from Limnephilid Caddis Flies

et al. 2001

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The Synthesis of (+)-Allopumiliotoxin 323B′

Tan¹,

Holmes²

2001

Chem. Eur. J.

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This paper describes the synthesis of (+)-allopumiliotoxin 323B' (1) using the intramolecular [3 + 2]-cycloaddition reaction of the (Z)-N-alkenylnitrone 4. This synthesis began with (R)-tert-butyl-3-hydroxy-pent-4-enoate [(R)-13] which was obtained by enzymatic resolution with Amano PS lipase. A series of manipulations gave intermediate 17 and in situ coupling with 4-benzoyloxybutanal lead to the (Z)-N-alkenylnitrone 4 which underwent an intramolecular [3 + 2]-cycloaddition reaction to give the isoxazolidine 3 as the major cycloadduct. Isoxazolidine 3 provided the piperidinone 24 which upon diastereofacial selective addition of MeMgBr gave the required tertiary alcohol 25. Formation of the indolizidine core 2 was achieved by an intramolecular S(N)2 reaction. The side chain was assembled from a Wittig reaction between the phosphorane 8 and the enantiomerically pure aldehyde 9. Further modifications afforded the aldehyde 7 which underwent an aldol condensation with the potassium enolate of the indolizidone core 2. Dehydration gave the enone 37 which was converted into the anti-diol 38 by intramolecular hydride reduction. Finally, deprotection of the BOM protecting group gave (+)-allopumiliotoxin 323B' (1).

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Pheromones, 65. Identification of the volatile components of the mandibular gland secretion of the ant Manica rubida: Structure elucidation, synthesis, and absolute configuration of Manicone

Cited by 25 publications

References 17 publications

A Novel Synthesis of Functionalized Tetrahydrofurans by an Oxa-Michael/Michael Cyclization of γ-Hydroxyenones

A Novel Synthesis of Functionalized Tetrahydrofurans by an Oxa-Michael/Michael Cyclization of γ-Hydroxyenones

Identification and Assignment of the Absolute Configuration of Biologically Active Methyl-Branched Ketones from Limnephilid Caddis Flies

The Synthesis of (+)-Allopumiliotoxin 323B′

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