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Publikováno v:
Journal of the American Chemical Society. 122:2749-2757
The ability of surfactant aggregate−H2O interfaces to control the regioselectivity of Diels−Alder reactions has been investigated. Cycloadditions of surfactant 1,3-dienes 2-[[3-(dimethyldodecylsilyl)-1,3-butadien-2-yl]thio]-N,N,N-trimethyl-1-etha
Publikováno v:
Journal of the American Chemical Society. 121:700-709
Enantioselective total syntheses of aloperine (1), N-methylaloperine (2), and N-allylaloperine (3) are reported. The central element of the synthetic strategy is an intramolecular Diels−Alder reaction in which the cycloaddends are tethered by a N-s
Publikováno v:
Journal of the American Chemical Society. 113:657-665
The intramolecular cycloaddition reactions of the tetraene ethers 10 and 17 and the triene ether 28 were investigated. Acetone-sensitized excitation of 10 led to three intramolecular [2 + 2] cycloadducts 11-13. However, CuOTf-catalyzed photolysis of
Publikováno v:
Journal of the American Chemical Society. 127:8292-8293
We describe a convergent, enantioselective synthesis of (-)-tetracycline (1) from benzoic acid (17 steps, 1.1% yield). Benzoic acid was transformed into the AB precursor 2 in 10 steps (11% yield), as previously described, and the latter compound was