A Short Stereoselective Synthesis of Cecropia Juvenile Hormone
نویسندگان
چکیده
منابع مشابه
A short stereoselective synthesis of cecropia juvenile hormone. Experimental details.
Experimental details are reported for a previously described synthesis of cecropia juvenile hormone.
متن کاملAbsolute configuration of Cecropia juvenile hormone.
The absolute configuration of the predominant Cecropia hormone, methyl 12,14-dihomojuvenate, has been determined to be methyl (E,E)-(10R,11S)-(+)-10,11-epoxy-7-ethyl-3,11-dimethyl-2, 6-tridecadienoate (I). The less abundant hormone, methyl 12-homojuvenate, can be presumed by analogy to have the corresponding 3,7,11-trimethyldienoate structure (II). The assignment has been established with micro...
متن کاملTotal synthesis of the racemic form of the second juvenile hormone (methyl 12-homojuvenate) from the cecropia silk moth.
Methyl cis-10-epoxy-3,7,11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-gamma-bromo-beta,beta-dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hormone (methyl 12-homojuvenate) isolated from the Cecropia silk moth. The biological activitie...
متن کاملShort Stereoselective Synthesis of the Phytophthora Universal Mating Hormone Alpha 1 using Lithiation/Borylation Reactions**
Alpha 1, the universal mating hormone of the virulent plant pathogen, Phytophthora, has been synthesized in 12 steps and 28% overall yield. Key C-C bond forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry at C11. Detailed analysis showed that the diastereomeric purity of the target...
متن کاملShort stereoselective synthesis of the Phytophthora universal mating hormone α1 using lithiation/borylation reactions.
The universal mating hormone α 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28 % overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric pu...
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ژورنال
عنوان ژورنال: Proceedings of the National Academy of Sciences
سال: 1970
ISSN: 0027-8424,1091-6490
DOI: 10.1073/pnas.67.3.1462