72598-35-7Relevant articles and documents
New synthesis of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne)
Zlokazov,Veselovsky
, p. 1600 - 1603 (2002)
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.
New synthesis of serricornin, the female sex pheromone of the cigarette beetle
Fujita, Ken,Mori, Kenji
, p. 1429 - 1433 (2001)
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.
Thiopyran route to polypropionates: An efficient synthesis of serricornin
Ward, Dale E.,Jheengut, Vishal,Beye, Garrison E.
, p. 8989 - 8992 (2006)
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.
Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations
Linne, Yannick,Sch?nwald, Axel,Wei?bach, Sebastian,Kalesse, Markus
supporting information, p. 7998 - 8002 (2020/06/09)
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.
Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone
Sabitha, Gowravaram,Srinivas, Chitti,Maruthi, Chittapragada,Yadav, Jhillu Singh
, p. 2071 - 2079 (2012/03/27)
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.
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
Masuda, Yui,Fujita, Ken,Mori, Kenji
, p. 1744 - 1750 (2007/10/03)
(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.
Versatile enantioselective synthesis of four diastereomers of serricornin, a sex pheromone of the cigarette beetle, using the SAMP/RAMP-hydrazone method
Job, Andreas,Nagelsdiek, Rene,Enders, Dieter
, p. 524 - 538 (2007/10/03)
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
The baker's yeast reduction of the β-keto aldehydes in the presence of a sulfur compound
Hayakawa, Ryuuichirou,Shimizu, Makoto
, p. 1298 - 1300 (2007/10/03)
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.
Asymmetric Synthesis of Serricornin via Boronic Esters
Matteson, Donald S.,Singh, Rajendra Prasad,Schafman, Bonnie,Yang, Jing-Jing
, p. 4466 - 4469 (2007/10/03)
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.
A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin
Chan, Philip C.-M.,Chong, J. Michael,Kousha, Karim
, p. 2703 - 2714 (2007/10/02)
(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%.
