Synthesis of the three isomeric components of San Jose scale pheromone

Alderdice, Margot; Spino, Claude; Weiler, Larry

doi:10.1016/s0040-4039(01)81133-3

Cited by 36 publications

(11 citation statements)

References 11 publications

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“…The structures of the three compounds, 5-7, were solved by spectroscopic methods (12) and confiied by synthesis (13). Following the preliminary communication of our work (14), two other syntheses of these compounds were reported (15). The first of these syntheses involved a regioselective allylic chlorination of the propionate esters of geraniol or nerol followed by reduction of the allylic halide to give 5 or 6 as shown in eq.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes

Alderdice¹,

Spino²,

Weiler³

1993

Can. J. Chem.

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The three isomeric components of the San Jose scale pheromone, 5-7, have been synthesized from a common P-keto ester intermediate. A study of the alkylation of the dianion of methyl acetoacetate with a series of alkylating agents with the same carbon skeleton has been carried out. The trisubstituted alkenes in 5 and 6 have been synthesized stereospecifically via a copper-catalyzed coupling of a methyl Grignard reagent with the E or Z en01 phosphate from the alkylated P-keto ester. In the case of the Z en01 derivative, the coupling reaction was carried out on the diethyl-and diphenylphosphates, and the en01 triflate. 'The diethyl en01 phosphate gave the highest stereoselectivity. The synthetic pheromones were attractive to San Jose scale in the field.MARGOT ALDERDICE, CLAUDE SPINO et LARRY WEILER. Can. J. Chem. 71, 1955Chem. 71, (1993. Utilisant un p-ceto ester commun comme intermediaire, on a synthetise les trois isomitres 5-7 de la pheromone du pou de San JosC. On a rCalisC une Ctude de I'alkylation du dianion de 1'acCtoacetate de mCthyle par une sCrie d'agents d'alcoylation ayant le m&me squelette carbone. On a synthCtisC les alcitnes trisubstituCs 5 et 6 d'une maniitre stCreospCcifique en faisant appel a un couplage catalysC par le cuivre d'un mCthyl magnesien avec le phosphate d'Cnol E ou Z obtenu B partir du p-ceto ester alcoyle. Dans le cas du dCrivC Cnolique Z, on a rCalisC la reaction de couplage sur les phosphates Cnoliques diCthyle et de diphenyle et sur le triflate Cnolique. Le phosphate Cnolique diethylique donne la meilleure sterCosClectivitC. Dans les champs, les phCromones de synthitse attirent le pou de San Jose.[Traduit par la redaction]

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Section: Introductionmentioning

confidence: 99%

The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes

Alderdice¹,

Spino²,

Weiler³

1993

Can. J. Chem.

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“…12 These, in turn, react stereospecifically in a substitution reaction with methylcuprates. 13 Thus, E,E -farnesol ( 14 ) was converted into β-keto ester 15 in 84% yield (over 2 steps). Execution of Casey’s and Weiler’s protocols followed by reduction of the ester with DIBAL-H provided E,E,Z -tetraprenyl alcohol 17 as the only stereoisomer observed and yields ranged from 30 to 50% over 5 steps.…”

Section: Resultsmentioning

confidence: 99%

“…Execution of Casey’s and Weiler’s protocols followed by reduction of the ester with DIBAL-H provided E,E,Z -tetraprenyl alcohol 17 as the only stereoisomer observed and yields ranged from 30 to 50% over 5 steps. 12,13 …”

Section: Resultsmentioning

confidence: 99%

Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics

et al. 2011

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We present a flexible, modular route to GlcNAc-MurNAc-oligosaccharides that can be readily converted into peptidoglycan (PG) fragments to serve as reagents for the study of bacterial enzymes that are targets for antibiotics. Demonstrating the utility of these synthetic PG substrates, we show that the tetrasaccharide substrate lipid IV (3), but not the disaccharide substrate lipid II (2), significantly increases the concentration of moenomycin A required to inhibit a prototypical PG-glycosyltransferase (PGT). These results imply that lipid IV and moenomycin A bind to the same site on the enzyme. We also show the moenomycin A inhibits the formation of elongated polysaccharide product but does not affect length distribution. We conclude that moenomycin A blocks PG-strand initiation rather than elongation or chain termination. Synthetic access to diphospholipid oligosaccharides will enable further studies of bacterial cell wall synthesis with the long-term goal of identifying novel antibiotics.

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“…For example, the stereoselective preparation of both geometrical isomers of enol phosphates from the corresponding b-keto esters has been reported. 8 We prepared the (E)-enol phosphate 13 (R = Ph) as the model compound in order to examine the coupling reaction (Scheme 4). The aldol reaction of the aldehyde 11 with the lithium enolate of methyl acetate afforded the desired product (89%), followed by Dess-Martin oxidation 9 to give the b-keto ester 12 (79%), which was treated with ClP(O)(OPh) 2 in the presence of triethylamine, providing the enol phosphate 13 (R = Ph), stereoselectively (87%).…”

Section: Introductionmentioning

confidence: 99%

Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

Hayashi

Nakada

2009

Tetrahedron Letters

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Synthesis of the three isomeric components of San Jose scale pheromone

Cited by 36 publications

References 11 publications

The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes

The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes

Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics

Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

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