62992-46-5Relevant articles and documents
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Bedoukian
, p. 1111,1112 (1971)
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Total synthesis of the antimicrobial fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid
Reyes, Elba D.,Carballeira, Nestor M.
, p. 1195 - 1198 (1997)
The antimicrobial marine fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid, recently identified in the phospholipids of the Caribbean gorgonian Eunicea succinea, and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid, initially identified in the phospholipids of the sponge Petrosia ficiformis, have been synthesized for the first time through a common synthetic route. A combination of alkyne-bromide coupling and Wittig reaction resulted in the best combination for assembling the Δ5,9 functionality in high yield and stereoselectivity.
Stereospecific synthesis of (4e,10z)-4,10-tetradecadienyl acetate, the major sex pheromone of apple leaf miner moth, phyllonorycter ringoniella
Awalekar, Ramchandra,Jagadhane, Kishor,Usmani, Shams,Salunkhe, Shilpa,Jamale, Dattatray,Hangirgekar, Shankar,Kolekar, Govind,Anbhule, Prashant
, p. 588 - 593 (2021/09/30)
The main component of the sex pheromone of many lepidopteran pests, (4E,10Z)-4,10-tetradecadienyl acetate (1) has been synthesized stereoselectively by using a simple route with 4-pentynol as a starting material. The stereoselective formation of the 4E double bond is based on the stereospecific reduction of internal alkyne with lithium aluminium hydride (LAH) while Wittig reaction was used to achieve 10Z double bond in the target pheromone component. The GC purity of the final acetate was achieved 97.87% while isomeric purities are more than 99%. The green chemistry principle shows a new concept towards the multistep pheromone synthesis via green metrics calculations.
Site-Selective trans-Hydrostannation of 1,3- and 1,n-Diynes: Application to the Total Synthesis of Typhonosides E and F, and a Fluorinated Cerebroside Analogue
Mo, Xiaobin,Letort, Aurélien,Ro?ca, Drago?-Adrian,Higashida, Kosuke,Fürstner, Alois
supporting information, p. 9667 - 9674 (2018/07/14)
Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the -OH group and the polarized [Ru-Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one -OH group to site-selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site-selectivity, whereas per-stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3-diyne substrate by two metal centers. The preparative relevance of site-selective trans-hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late-stage modification of a bioactive target compound.
