- Straightforward preparation of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal
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A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-hep-tadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).
- Petroski, Richard J.
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- Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: Total synthesis of epiplakinic acid F
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The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared. This journal is the Partner Organisations 2014.
- Tian, Xiang-Yin,Han, Jian-Wei,Zhao, Qiong,Wong, Henry N. C.
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p. 3686 - 3700
(2014/06/09)
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- Total synthesis of amaminol A: Establishment of the absolute stereochemistry
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The first synthetic route to amaminol A with use of an organocatalytic intramolecular Diels-Alder reaction is reported. The absolute stereochemistry is proven with a crystallographic image of a cyclic carbamate of amaminol A.
- Kumpulainen, Esa T. T.,Koskinen, Ari M. P.,Rissanen, Kari
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p. 5043 - 5045
(2008/03/27)
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- Synthesis of plastoquinone derivatives with different structures of the side chain
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Two schemes for the synthesis of plastoquinone derivatives with ω-substituted alkyl side chains have been developed, based on radical alkylation of 2,3-dimethyl-1,4-benzoquinone with ω-substituted carboxylic and/or dicarboxylic acids in the presence of S2O82- and Ag+.In Scheme 1, radical alkylation of 2,3-dimethyl-1,4-benzoquinone with 11-bromoundecanoic acid, in the presence of (NH4)2S2O8 and AgNO3, gave 2,3-dimethyl-5-(10-bromodecyl)-1,4-benzoquinone, which, after hydration, gave 2,3-dimethyl-5-(10-hydroxydecyl)-1,4-benzoquinone.Esterification of 2,3-dimethyl-5-(10-hydroxydecyl)-1,4-benzoquinone with different acyl chlorides gave 2,3-dimethyl-5-(10-acyloxydecyl)-1,4-benzoquinone.In Scheme 2, radical alkylation of 2,3-dimethyl-1,4-benzoquinone with adipic acid, in the presence of K2S2O8 and AgNO3, gave 2,3-dimethyl-5-(4-carboxybutyl)-1,4-benzoquinone, which was converted to 2,3-dimethyl-5--1,4-benzoquinone by esterification with different alcohols in the presence of dicyclohexylcarbodiimide. 2,3-Dimethyl-5-(8-carboxyoctyl)-1,4-benzoquinone and 2,3-dimethyl-5--1,4-benzoquinone were similarly synthesized from 2,3-dimethyl-1,4-benzoquinone and sebacic acid.Plastoquinone derivatives having different kinds of double bonds in the side chain with and without a 6-methyl group were synthesized from 2,3,5-trimethyl-1,4-benzoquinone and 2,3-dimethyl-1,4-benzoquinone by successive reactions with (1) NaBH4; (2) KHSO4, different kinds of allylic alcohols; (3) Ag2O.The allylic alcohols were prepared from their corresponding aldehydes by reduction with NaBH4. 2,3,6-Trimethyl-1,4-benzoquinone by radical methylation with acetic acids in the presence of K2S2O8 + AgNO3.
- Liu, Benli,Gu, Lianquan,Zhang, Jingling
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p. 104 - 110
(2007/10/02)
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- Total Synthesis of the Potent Mutagen (S)-3-(Dodeca-1,3,5,7,9-pentaenyloxy)propane-1,2-diol
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A total synthesis of the mutagenic (S)-3-(dodeca-1,3,5,7,9-pentaenyloxy)propane-1,2-diol (1) from (R)-glycerol acetonide (2), potassium glutaconate (6), and the diphenylphosphine oxide (11) is reported.
- Nicolaou, K. C.,Zipkin, Robert,Tanner, David
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p. 349 - 350
(2007/10/02)
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- SYNTHESIS OF RACEMIC FECAPENTAENE-12, A POTENT MUTAGEN FROM HUMAN FECES, AND ITS REGIOISOMER
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Racemic fecapentaene-12 and its regioisomer 2-(1,3,5,7,9-dodecapentaenyloxy)-1,3-propanediol (2) have been synthesized.The latter compound is comparably mutagenic to 1.
- Gunatilaka, A. A. Leslie,Hirai, Nobuhiro,Kingston, David G. I.
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p. 5457 - 5460
(2007/10/02)
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