Radical mediated stereoselective synthesis of meso-7,11-dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper

Nagano, Hajime; Kuwahara, Rie; Yokoyama, F.

doi:10.1016/j.tet.2007.06.027

Cited by 6 publications

(7 citation statements)

References 21 publications

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“…Table 3 shows methyl-branched secondary alcohols and their esters , which act as pheromones in insects and a mite. Four secondary alcohols (43)(44)(45)(46) with one methyl branch in a C 7 -C 9 main chain have been identied as an aggregation pheromone of insects in Coleoptera. Their hydroxyl groups are located at different 3-5-positions; 43-45 are considered to be the same 5-hydroxy compounds when their positions are counted from the opposite chain terminal.…”

Section: Secondary Alcohols and Their Estersmentioning

confidence: 99%

“…Some a-methyl secondary alcohols have been synthesized from 2,3-epoxyalkan-1-ol (S11). The (2S,3R)-isomer of the C 5 epoxy synthon (S11a, R ¼ Me) prepared by the Sharpless asymmetric epoxidation of (Z)-2-pentan-1-ol using (+)-DET was methylated using AlMe 3 to yield the (2R,3S)-3-methyl-1,2-diol, which was converted into the (3S,4S)-isomer of the 4-hydroxy-3methyl pheromone (44). 135 The methylating reagent selectively attacked a carbon at the 3-position behind the epoxy ring.…”

Section: Employment Of Chiral Sourcesmentioning

confidence: 99%

“…(R)-28 and (S)-69 were synthesized using similar reactions. 86,209 Furthermore, a-methyl secondary alcohols (44)(45)(46) were synthesized by asymmetric aldol condensation using an imide of another chiral oxazolidinone (R-1-4e). 137 The boron enolate derivative from the imide was treated with n-pentanal or n-butanal to afford syn adducts.…”

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

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Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

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Insect pheromones are some of the most interesting natural products because they are utilized for interspecific communication between various insects, such as beetles, moths, ants, and cockroaches. A large number of compounds of many kinds have been identified as pheromone components, reflecting the diversity of insect species. While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques. Furthermore, their stereoselective syntheses have been achieved by employing trustworthy chiral sources and ingenious enantioselective reactions. The information has been reviewed here not only to make them available for new research but also to understand the characteristic chemical structures of the chiral pheromones. Since biosynthetic studies are still limited, it might be meaningful to examine whether the structures, particularly the positions and configurations of the branched methyl groups, are correlated with the taxonomy of the pheromone producers and also with the function of the pheromones in communication systems.

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Section: Secondary Alcohols and Their Estersmentioning

confidence: 99%

Section: Employment Of Chiral Sourcesmentioning

confidence: 99%

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

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Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

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“…Nagano et al [11] presented a stereoselective synthesis of 1. Starting from ethyl bromomethacrylate (A), they prepared diethyl 4-benzyloxy-2,6-dimethyleneheptanedioate (B), which was used in a diastereoselective chelationcontrolled radical reaction with pentyl iodide in the key step (Scheme 1).…”

Section: Meso-711-dimethylheptadecane (1)mentioning

confidence: 99%

“…[(6Z,9Z,11S,12S)-trans-11,12-epoxy-6,9heneicosadiene (11)] is the pheromone of the tussock moth Orgyia postica, a pest of mango and litchi trees in Japan [31]. A multigram synthesis of the trans-epoxide pheromone, starting from diethyl L-tartrate was carried out by Fernandes [32], employing Wittig olefinations and the stereoselective conversion of an intermediate diol to the epoxide (Scheme 10).…”

Section: Posticlurementioning

confidence: 99%