Author
Leah M. Gayo
Bio: Leah M. Gayo is an academic researcher from University of California, Irvine. The author has contributed to research in topics: Organolithium reagent & Reagent. The author has an hindex of 2, co-authored 4 publications receiving 76 citations.
Topics: Organolithium reagent, Reagent, Heteroatom
Papers
More filters
TL;DR: In this article, a potentially general regiospecific synthesis of benzo- and naphthoquinones is described, which starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 9 upon sequential treatment with an organolithium reagent and then BF 3 etherate or TFAA in THF/methanol.
Abstract: A potentially general regiospecific synthesis of benzo- and naphthoquinones is described. This method starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 9 upon sequential treatment with an organolithium reagent and then BF 3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5.Addition of an alkynyl-,alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl-4-alkenyl- or 4-aryl-4-hydroxycyclobutenones 7-9 and these readly rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene.In a similar fashion,15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones
48 citations
TL;DR: In this article, a new synthetic route to highly substituted cyclobutenones is reported, which involves the 1,6-addition of both heteroatom-and carbon-based nucleophiles to 4,4-dimethoxy-3-ethenyl-2-methyl-cyclobuten-1-one (8) to give further functionalized cyclobutenedione monoketals.
Abstract: A new synthetic route to highly substituted cyclobutenones is reported. This involves the 1,6-addition of both heteroatom- and carbon-based nucleophiles to 4,4-dimethoxy-3-ethenyl-2-methyl-cyclobuten-1-one (8) to give further functionalized cyclobutenedione monoketals. These ketals function as precursors to quinones as illustrated by the synthesis of the natural benzofuranosesquiterpene 23
28 citations
TL;DR: In this paper, a potentially general regiospecific synthesis of benzo- and naphthoquinones is described, which starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 9 upon sequential treatment with an organolithium reagent and then BF 3 etherate or TFAA in THF/methanol.
Abstract: A potentially general regiospecific synthesis of benzo- and naphthoquinones is described. This method starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 9 upon sequential treatment with an organolithium reagent and then BF 3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5.Addition of an alkynyl-,alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl-4-alkenyl- or 4-aryl-4-hydroxycyclobutenones 7-9 and these readly rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene.In a similar fashion,15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones
TL;DR: In this article, a new synthetic route to highly substituted cyclobutenones is reported, which involves the 1,6-addition of both heteroatom-and carbon-based nucleophiles to 4,4-dimethoxy-3-ethenyl-2-methyl-cyclobuten-1-one (8) to give further functionalized cyclobutenedione monoketals.
Abstract: A new synthetic route to highly substituted cyclobutenones is reported. This involves the 1,6-addition of both heteroatom- and carbon-based nucleophiles to 4,4-dimethoxy-3-ethenyl-2-methyl-cyclobuten-1-one (8) to give further functionalized cyclobutenedione monoketals. These ketals function as precursors to quinones as illustrated by the synthesis of the natural benzofuranosesquiterpene 23
Cited by
More filters
TL;DR: Transformation of Cyclobutane Derivatives inNatural Product Syntheses: A Review of the Transformations in Organic Syntheses.
Abstract: I. Introduction 1485II. Scope of This Review 1485III. Transformations of Cyclobutane Derivatives inOrganic Syntheses1486A. Ring-Opening Reactions 1486B. Ring-Contraction Reactions 1493C. Ring-Expansion Reactions 14951. Five-Membered Rings 14952. Six-Membered Rings 15093. Seven-Membered Rings 15174. Eight-Membered Rings 15215. Nine-Membered Rings 1523IV. Transformations of Cyclobutane Derivatives inNatural Product Syntheses1524A. Ring-Opening Reactions 1524B. Ring-Expansion Reactions 15261. Five-Membered Rings 15262. Six-Membered Rings 15293. Seven-Membered Rings 15324. Eight-Membered Rings 1533V. Conclusion 1534VI. Acknowledgments 1534VII. References 1534
517 citations
TL;DR: Recently, the scope of organocopper chemistry has been broadened significantly by the development of 1,6-, 1,8-,1,10-, and 1,12-addition reactions, as well as of 1-5-substitution reactions of multiply unsaturated substrates which often contain at least one triple bond.
70 citations
62 citations
TL;DR: 1,6-Addition of aryl Grignard reagents to 2,4-dienoates or -dienamides was nicely catalyzed by iron salt to give 5-aryl-3-enoates or the corresponding amides in a highly regio- and stereoselective manner.
57 citations
TL;DR: A wide variety of 3-alkyne-1,2-diols have been found to undergo exceptionally clean 5-endo-dig cyclisations followed by dehydration at ambient temperature to give the corresponding furans in essentially quantitative yields when exposed to 10 ǫ% of 10% w/w silver nitrate absorbed on silica gel.
52 citations