A bridgehead carbocation fragmentation leading to the taxane AB ring system
01 Jan 1993-Synlett (© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.)-Vol. 1993, Iss: 01, pp 71-72
About: This article is published in Synlett.The article was published on 1993-01-01. It has received 12 citations till now. The article focuses on the topics: Carbocation & Ring (chemistry).
Citations
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
259 citations
01 Feb 2014
TL;DR: The use of hypervalent iodine reagents such as 2-iodoxybenzoic acid (IBX) in α,β-dehydrogenation reactions has grown significantly, as have catalytic dehydrogenation methods, such as Pd-catalyzed methods capable of O 2 or other desirable stoichiometric oxidants as discussed by the authors.
Abstract: α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. This chapter summarizes different oxidation methods available for dehydrogenation adjacent to carbonyl groups to access α,β-unsaturated carbonyl compounds. Historically important stoichiometric methods include sequential halogenation/dehydrohalogenation, elimination reactions that use sulfur and selenium reagents, and dichlorodicyanoquinone (DDQ)-mediated dehydrogenation. The use of hypervalent iodine reagents, such as 2-iodoxybenzoic acid (IBX), in α,β-dehydrogenation reactions has grown significantly, as have catalytic dehydrogenation methods, such as Pd-catalyzed methods capable of O 2 or other desirable stoichiometric oxidants. An overview of each of these methods is presented, together with selected synthetic applications. The relative merits of the individual methods are also considered.
34 citations
TL;DR: Key to the cascading ring-expansion process is an unprecedented intramolecular alkyne analogue of the de Mayo reaction.
Abstract: Embedded medium-sized carbacycles and cyclohepta[b]indoles occur frequently as scaffold elements in natural products and bioactive compounds. Described herein is a conceptionally novel photochemically triggered cascade process to these scaffolds. Key to the cascading ring-expansion process is an unprecedented intramolecular alkyne analogue of the de Mayo reaction.
25 citations
TL;DR: In this article, an efficient domino cross-enyne metathesis/intramolecular Diels-Alder reaction was demonstrated for the construction of a bicyclo[5.3.1]undecene.
24 citations