Showing papers by "Philip L. Fuchs published in 1993"
TL;DR: In this paper, aryl iodides with 5% tetrakis(triphenylphosphine)palladium[O] in the presence of silver nitrate and triethylamine in acetonitrile at reflux effects intramotecular conjugate-addition/reductive elimination to generate an annulated vinyl sulfone.
31 citations
TL;DR: Tetramethylguanidinium azide was used in the quantitative conversion of glycosyl halides 1 − 6 to the corresponding glycoly azides 7 − 12 as discussed by the authors.
28 citations
TL;DR: In this article, the synthesis of cis-fused bicyclic ethers by intramolecular conjugate addition of vinyl lithium and organopalladium reagents to cyclohexenyl/pentenyl moiety of vinyl sulfones is described.
19 citations
TL;DR: In this article, a-hydroxy naphthoate esters are shown to be capable of undergoing intramolecular alkylation at carbon as well as at both oxygen centers.
Abstract: α-Hydroxy naphthoate esters are shown to be capable of undergoing intramolecular alkylation at carbon as well as at both oxygen centers. Basic reaction conditions favor intramolecular oxygen alkylation of the phenol moiety in addition to intramolecular carbon alkylation leading to spirolactones. Chemistry in neutral or acidic media appears to proceed via γ-oxo ketene acetal intermediates that are converted to products derived from addition of water followed by cleavage of the resultant orthoacid. γ-Oxo ketene acetal intermediates derived from naphthoate esters are at least 40 times more reactive than those derived from simple β-keto esters. These studies give credence to the proposal that the a-hydroxy naphthoate moiety in neocarzinostatin is capable of participation are discussed
17 citations
TL;DR: In this article, 5-(Tributylstannyl)-1-penten-3-one is prepared in 50% overall yield from the readily available 3-((triethylsilyl)oxy)-1,4-pentadiene.
Abstract: 5-(Tributylstannyl)-1-penten-3-one is prepared in 50% overall yield from the readily available 3-((triethylsilyl)oxy)-1,4-pentadiene. Use of this reagent in the Robinson annulation reaction provides α-stannylmethyl enones in very good yields. Cerium-mediated 1,2 reduction followed by acylation affords the corresponding allylic acetate. Both classes of compounds undergo specific S E 2' oxidation with lead tetraacetate, mCPBA, and halogenating agents at the tertiary center of the allylic stannane to initially afford exocyclic olefins. Rearrangement of the allylic acetates and allylic halides subsequently provides the isomeric endocyclic enone bearing a functionalized methyl group. Further chemistry includes Birch reduction of an α-stannylmethyl enone to a satured α-stannylmethyl ketone as well as application of the Robinson annulation strategy to a hydrophenanthrene system. Attempts to effect additional Robinson annulation reactions on substrates already bearing the tributylstannane moiety either fail or proceed in very poor yield
11 citations
TL;DR: In this paper, the photocyclization of aryl vinyl sulfones at 254 nm was described, which proceed stereoselectively, and was shown to work well in the case of N-s.
9 citations
TL;DR: Tetramethylguanidinium azide was used in the quantitative conversion of glycosyl halides 1 − 6 to the corresponding glycoly azides 7 − 12 as discussed by the authors.
Abstract: Tetramethylguanidinium azide was used in the quantitative conversion of glycosyl halides 1 – 6 to the corresponding glycosyl azides 7 – 12. The stereoselective reactions occurred with complete inversion at the anomeric centers.
1 citations
1 citations