Enantioselective synthesis of (−)-serricornin, a sex pheromone of a female cigarette beetle (Lasioderma serricorne F.)

Miyashita, Masaaki; Toshimitsu, Y.; Shiratani, Tomonori; Irie, Hiroshi

doi:10.1016/s0957-4166(00)80362-6

Cited by 22 publications

(3 citation statements)

References 14 publications

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“…Of several methods available to prepare the target chiral o-methyl secondary alcohols, the Sharpless asymmetric epoxidation combined with diastereoselective ring opening was the most appealing (Gao et al, 1987;Hill et al, 1985; for use of trimethylaluminum and organocuprates: Pfaltz and Mattenberger, 1982;Suzuki et al, 1982;Takano et al, 1989;Vaccaro et al, 1992;Miyashita et al, 1993). This strategy allowed the use of inexpensive reagents and the synthesis of all four stereoisomers from the same starting material.…”

Section: Resultsmentioning

confidence: 99%

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

et al. 1994

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There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil,Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by maleR. phoenicis and maleR. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, withR. phoenicis in Côte d'Ivoire andR. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

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Section: Resultsmentioning

confidence: 99%

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

et al. 1994

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“…They also reported the formal synthesis of protomycinolide IV 7 [ 139 ]. In addition, several other fragments and/or natural products have been prepared by Miyashita et al For instance, the following polypropionate-containing-natural products: (−)-serricornin 23 [ 140 ], rifamycins 15 [ 141 ], streptovaricin U 16c [ 142 ], protostreptovaricin I and II ( 16c-d ) [ 142 ], scytophycin C 11 [ 143 , 144 , 145 ], swinholides A-C 14a-c [ 146 ], tedanolide 9 [ 147 ], lepranthin 8 [ 148 ], and venturicidins 10a-c [ 149 ] were all prepared from epoxides and trimethylaluminum for the regio- and stereospecific methylation ( Figure 11 , bottom). It is worth noting that Miyashita also reported the use of m -chloroperoxybenzoic acid ( m CPBA) for highly stereoselective epoxidations of chiral allylic alcohols [ 150 ] and organoselenium reagents for a chemoselective reduction of epoxides [ 151 ]; both important methodologies for the synthesis of polypropionates.…”

Section: Polypropionate Epoxide-based Approachesmentioning

confidence: 99%

Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products

Rodríguez-Berríos

Isbel

Bugarin

2023

IJMS

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Polypropionate units are a common structural feature of many of the natural products in polyketides, some of which have shown a broad range of antimicrobial and therapeutic potential. Polypropionates are composed of a carbon skeleton with alternating methyl and hydroxy groups with a specific configuration. Different approaches have been developed for the synthesis of polypropionates and herein we include, for the first time, all of the epoxide-based methodologies that have been reported over the years by several research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. Several syntheses of polypropionate fragments and natural products that employed epoxides as key intermediates have been described and summarized in this review. These synthetic approaches involve enatio- and diastereoselective synthesis of epoxides (epoxy-alcohols, epoxy-amides, and epoxy-esters) and their regioselective cleavage with carbon and/or hydride nucleophiles. In addition, we included a description of the isolation and biological activities of the polypropionates and related natural products that have been synthetized using epoxide-based approaches. In conclusion, the epoxide-based methodologies are a non-aldol alternative approach for the construction of polypropionate.

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“…For the synthesis of the already known (2R,3S)-4-benzyloxy-2,3-epoxybutanol 52 (6.2), the Katsuki-Sharpless asymmetric epoxidation 51 Review of serricornin and, sex pheromone of the cigarette beetle (Lasioderma serricorne), 6.1, was used 53 . The general strategy for obtaining the pheromone included oxidation of the hydroxy group in 6.2 and Horner-Emmons reaction of the resulting aldehyde giving epoxyhexenoate 6.3, the methylation of which with trimethylaluminum led to the alcohol 6.4.…”

Section: Ketonesmentioning

confidence: 99%

Syntheses of Insect Sex Pheromones. A Review of the Literature 1990-1998

Koutek

Streinz

Romaňuk

1998

Collect. Czech. Chem. Commun.

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Enantioselective synthesis of (−)-serricornin, a sex pheromone of a female cigarette beetle (Lasioderma serricorne F.)

Cited by 22 publications

References 14 publications

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products

Syntheses of Insect Sex Pheromones. A Review of the Literature 1990-1998

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