- New synthesis of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne)
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A new approach to the total synthesis of serricornin, the sex pheromone of the cigarette beetle, based on readily available (4S,5E)-4-methyhept-5-enenitrile was implemented.
- Zlokazov,Veselovsky
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- New synthesis of serricornin, the female sex pheromone of the cigarette beetle
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Serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the female sex pheromone of Lasioderma serricorne, was synthesized by starting from (2S,4S)-2,4-dimethyl-1,5-pentanediol that had been obtained by lipase-catalyzed enantiomer separation of its racemate.
- Fujita, Ken,Mori, Kenji
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- Thiopyran route to polypropionates: An efficient synthesis of serricornin
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The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one] , a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective LisBu3BH reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.
- Ward, Dale E.,Jheengut, Vishal,Beye, Garrison E.
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- Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations
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anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed.
- Linne, Yannick,Sch?nwald, Axel,Wei?bach, Sebastian,Kalesse, Markus
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supporting information
p. 7998 - 8002
(2020/06/09)
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- Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone
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The synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone is described as their acetates using a desymmetrization strategy as well as an Evans syn aldol strategy.
- Sabitha, Gowravaram,Srinivas, Chitti,Maruthi, Chittapragada,Yadav, Jhillu Singh
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p. 2071 - 2079
(2012/03/27)
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- Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus
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(4R,6S,7R)-7-Hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5- dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus, as well as their (4R,6S,7S)-and (3R,5S,6S)-isomers were synthesized from (2R,4S,5R)- and (2R,4S,5S)2,4-dimethyl-5-heptanolide, respectively.
- Masuda, Yui,Fujita, Ken,Mori, Kenji
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p. 1744 - 1750
(2007/10/03)
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- Versatile enantioselective synthesis of four diastereomers of serricornin, a sex pheromone of the cigarette beetle, using the SAMP/RAMP-hydrazone method
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Serricornin is a female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-syn-isomers of serricornin, including the natura
- Job, Andreas,Nagelsdiek, Rene,Enders, Dieter
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p. 524 - 538
(2007/10/03)
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- The baker's yeast reduction of the β-keto aldehydes in the presence of a sulfur compound
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Improved enantio- and diastereoselectivity was achieved in the baker's yeast reduction of β-keto aldehyde derivatives using a sulfur compound as an additive. The resulting enantiomerically pure diol was transformed into serricornin, a sex pheromone of the cigarette beetle.
- Hayakawa, Ryuuichirou,Shimizu, Makoto
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p. 1298 - 1300
(2007/10/03)
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- Asymmetric Synthesis of Serricornin via Boronic Esters
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Highly stereoselective boronic ester chemistry has been used for the synthesis of (4S,6S,7S)-7- hydroxy-4,6-dimethylnonanone (1), the pheromone of the cigarette beetle. 2-Bromo-1-butene (8) was made from 1-butyne via bromoboration and protodeboronation, and was converted to 1-ethylethenylmagnesium bromide. (R,R)-1,2-Dicyclohexyl-1,2-ethanediol ["(R)-DICHED"] methylboronate was treated with (dichloromethyl)lithium to yield (R)-DICHED (S)-1-chloroethylboronate (9), which with 1-ethylethenylmagnesium bromide yielded (R)-DICHED (R)-(2-ethyl-1-methyl-2- propenyl)boronate (10). Further chain extensions with (chloromethyl)lithium, (dichloromethyl)- lithium followed by methylmagnesium bromide, and (dichloromethyl)lithium followed by ethyl- magnesium bromide completed assembly of the carbon skeleton. Deboronation with hydrogen peroxide yielded (3S,5S,6S)-2-ethyl-3,5-dimethylocten-6-ol (14), which with osmium tetraoxide and sodium periodate yielded 1.
- Matteson, Donald S.,Singh, Rajendra Prasad,Schafman, Bonnie,Yang, Jing-Jing
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p. 4466 - 4469
(2007/10/03)
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- A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin
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(4RS,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone (serricornin and its C4- epimer) may be prepared from oxazolidinone 5 in 8 steps with an overall yield of 33%.
- Chan, Philip C.-M.,Chong, J. Michael,Kousha, Karim
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p. 2703 - 2714
(2007/10/02)
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- Enantioselective Synthesis of (-)-Serricornin, a Sex Pheromone of a Female Cigarette Beetle (Lasioderma serricorne F.)
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(-)-Serricornin, a sex pheromone of a cigarette beetle (Lasioderma serricorne F.), has been synthesized highly stereoselectively starting from (Z)-4-benzyloxy-2-buten-1-ol by employing the Katsuki-Sharpless asymmetric epoxidation and two stereospecific me
- Miyashita, Masaaki,Toshimitsu, Yuuko,Shiratani, Tomonori,Irie, Hiroshi
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p. 1573 - 1578
(2007/10/02)
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- Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes
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Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.
- Shimizu,Hayashi,Ide,Oshima
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p. 2991 - 2998
(2007/10/02)
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- A short stereoselective synthesis of (-)-serricornin
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Palladium-catalyzed reduction of (+)-(E)-(6S,7S)-4,6-dimethyl-6,7-epoxy-4-nonen-3-one with formic acid gave (-)-(E)-(6S,7S)-4,6-dimethyl-7-hydroxy-4-nonen-3-one, which was hydrogenated to give (-)-serricornin.
- Shimizu,Hayashi,Oshima
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p. 4757 - 4758
(2007/10/02)
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- AN EFFICIENT AND STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SERRICORNINE
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An efficient and stereoselective total synthesis of (+/-)-serricornine (1) the sex pheromone produced by the female cigarette beetle Lasioderma serricorne F, is described. (3SR,5SR,6SR)-6-Ethyltetrahydro-3,5-dimethyl-2H-pyran-2-one (10) is prepared in 65percent yield through lactonization of a 1:1 mixture of C-2 epimrs of the corresponding esters.
- Pilli, R. A.,Mutra, M. M.
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p. 981 - 994
(2007/10/02)
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- SYNTHESES OF OPTICALLY ACTIVE INSECT PHEROMONES, -2-METHYL-5-HEXANOLIDE, -3,11-DIMETHYL-2-NONACOSANONE, AND SERRICORNIN
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Three insect pheromones, (2R,5S)-2-methyl-5-hexanolide, (3S,11S)-3,11-dimethyl-2-nonacosanone, and serricornin, were synthesized in optically pure forms by using newly developed asymmetric reactions as key steps.
- Katsuki, Tsutomu,Yamaguchi, Masaru
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p. 651 - 654
(2007/10/02)
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- A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle
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Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.
- Mori, Kenji,Watanabe, Hidenori
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p. 3423 - 3428
(2007/10/02)
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- SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN
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The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by
- Mori, Kenji,Nomi, Hiroko,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
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p. 3705 - 3712
(2007/10/02)
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- A STEREOSELECTIVE SYNTHESIS OF "NATURAL" (4S,6S,7S)-SERRICORNIN, THE SEX PHEROMONE OF CIGARETTE BEETLE, FROM LEVOGLUCOSENONE
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The natural stereoisomer of serricornin was synthesized stereoselectively from levoglucosenone.This firmly established the absolute stereochemistry of serricornin to be 4S,6S,7S.A short synthesis of (-)-δ-multistriatin was also reported.
- Mori, Masataka,Chuman, Tatsuji,Kato, Kunio,Mori, Kenji
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p. 4593 - 4596
(2007/10/02)
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- DETERMINATION OF THE ABSOLUTE CONFIGURATION AT C-6 AND C-7 SERRICORNIN (4,6-DIMETHYL-7-HYDROXY-3-NONANONE), THE SEX PHEROMONE OF THE CIGARETTE BEETLE
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The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 7S) by synthesizing its (6R, 7S)-erythro and (6R, 7R)-threo isomers.
- Mori, Kenji,Nomi, Hiroko /nee Iwasawa/,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
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p. 1127 - 1130
(2007/10/02)
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