Total synthesis of (-)-spinosyn A
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چکیده
منابع مشابه
Total synthesis of (-)-spinosyn A.
A convergent, highly stereoselective total synthesis of (-)-spinosyn A (1) is described. Key features of the synthesis include the transannular Diels-Alder reaction of macrocyclic pentaene 11 and the transannular Morita-Baylis-Hillman cyclization of 12 that generates tetracycle 26. The total synthesis of (-)-spinosyn A was completed by a sequence involving the highly beta-selective glycosidatio...
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The concept of modern crop protection demands for a continuous supply of new or modified established pesticides to avoid the development of serious resistances. Recent reports on the insecticidal spinosyns 1 and 2 show that also this class of pest managing agents is increasingly exposed to the formation of resistances. The synthesis of new derivatives is therefore highly desirable. We describe ...
متن کاملPseudoaglycone of Spinosyn A
THE TITLE COMPOUND [SYSTEMATIC NAME: 9-ethyl-13-hy-droxy-14-methyl-2-(3,4,5-trimeth-oxy-6-methyl-tetra-hydro-2H-pyran-2-yl-oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodeca-hydro-1H-as-indaceno[3,2-d][1]oxacyclo-dodecine-7,15(2H,5aH)-dione], C(33)H(50)O(9), was obtained by hydrolysis of Spinosyn A. The fused cyclo-pentene ring adopts a twisted conformation, while the fused cyclo-hexene and cyclo-p...
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[reaction: see text] Spinosyn G was isolated in the late 1980s as a minor component from the broth of our potent, fermentation-derived insecticide spinosad. Its structure was then tentatively identified as 5' '-epispinosyn A (3) on the basis of (1)H and (13)C NMR data, but the 4' '-epi compound 4 could not be conclusively ruled out with the data available. Described herein are unambiguous synth...
متن کاملTotal Synthesis of Lycopalhine A.
The total synthesis of lycopalhine A has been accomplished. The synthesis features construction of the tricyclic system via cleavage of a cyclopropane ring and an ensuing intramolecular Michael addition, stereoselective introduction of a 2-aminoethyl moiety via a reaction of allyltrimethylsilane to a sulfonyliminium ion, and a stereoselective intramolecular aldol reaction.
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ژورنال
عنوان ژورنال: Proceedings of the National Academy of Sciences
سال: 2004
ISSN: 0027-8424,1091-6490
DOI: 10.1073/pnas.0401247101