- STEREOSELECTIVE SYNTHESIS OF NATURAL (4S,6S,7S)-SERRICORNIN STARTING WITH (3S,4S)-4-HYDROXY-3-METHYL-1-HEXENE
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(4S,6S,7S)-Serricornin has been synthesized in three steps starting with (3S,4S)-4-hydroxy-3-methyl-1-hexene.
- Takeda, Yoshiyuki,Kobayashi, Yuichi,Sato, Fumie
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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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- 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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p. 8989 - 8992
(2007/10/03)
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- Synthesis of a biologically active analog of the sex pheromone of cigarette beetle (Lasioderma serricorne)
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A simple synthesis of a diastereomeric mixture of 7-hydroxy-4,6- dimethylnonan-3-ones was carried out. In the biological action, it is an analog of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne).
- Lozanova,Stepanov,Veselovsky
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p. 1254 - 1257
(2007/10/03)
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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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- 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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p. 1600 - 1603
(2007/10/03)
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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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p. 1429 - 1433
(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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- 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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- 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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- DIASTEREO- AND ENANTIOSELECTIVE PREPARATION OF β-ALKYLHOMOALLYLIC ALCOHOLS SYNTHESIS OF SERRICORNIN AND CORYNOMYCOLIC ACID
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A new and efficient method for the preparation of four possible stereoisomers of β-alkylhomoallylic alcohols 1 has been developed which is based on the diastereoselective addition of nucleophiles to optically active α-alkyl-β-trimethylsilyl-β,γ-unsaturate
- Kobayashi, Yuichi,Kitano, Yasunori,Takeda, Yoshiyuki,Sato, Fumie
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p. 2937 - 2944
(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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- ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL; SYNTHESIS OF SERRICORNIN
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Several electrophilic lactonization procedures have been explored as a means of functionalizing olefinic carboxylic acids with relative asymmetric induction.Iodolactonization of δ,ε-unsaturated acids under conditions of thermodynamic control exhibits good
- Bartlett, Paul A.,Richardson, David P.,Myerson, Joel
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p. 2317 - 2327
(2007/10/02)
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- Stereoselective Synthesis of Alcohols, XVIII. - Synthesis of (3S,4S)-4-Methyl-3-heptanol and of (5S,6S)-Anhydroserricornin
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Yeast reduction of methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate (5) led to the β-hydroxy ester 6 of 98percent diastereomeric and ca. 85percent enantiomeric purity. 6 was converted into enantiomerically pure anti-4-methyl-3-heptanol (4) and via the key intermediate 11 into enantiomerically pure anhydroserricornin (3).
- Hoffmann, Reinhard W.,Ladner, Wolfgang,Helbig, Wilfried
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p. 1170 - 1179
(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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- SYNTHESIS OF 6S,7S-ANHYDRO-SERRICORNINE.
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Diastereoselective and enantioselective reduction of the β-ketoester 3 by yeast to 4 provided the chiral starting material for a synthesis of 4RS,6S,7S-serricornine, having the same configuration as the natural product.This material was converted into optically active and diastereomerically pure 6S,7S-anhydro-serricornine (2).
- Hoffmann, Reinhard W.,Helbig, Wilfried,Ladner, Wolfgang
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p. 3479 - 3482
(2007/10/02)
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