Anion Relay Chemistry:  An Effective Tactic for Diversity Oriented Synthesis

Smith, Iii and Amos B.; Xian, Ming

doi:10.1021/ja057059w

Cited by 110 publications

(40 citation statements)

References 13 publications

(9 reference statements)

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“…Sequential dithiane-epoxide couplings can produce 1,5-diols with great versatility and efficiency, exploiting Brook rearrangement for in situ carbanion relay in a method first introduced by Smith and Boldi [44]. For example, the anti-anti 1,5,9-triol relationship in 71 was rapidly established via a three-component coupling [45]. Numerous methods for removal of the dithiane may potentially be applied in order to adapt this anion relay chemistry to 1,5-polyol natural products.…”

Section: Resultsmentioning

confidence: 99%

1,5-Polyols: Challenging motifs for configurational assignment and synthesis

Friestad

Sreenilayam

2011

Pure and Applied Chemistry

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Despite the well-established methods for stereochemical assignments and synthesis of 1,3-diols, the corresponding 1,5-diols and -polyols present specific challenges which remain unsolved. This article highlights some new strategies and methodologies specifically designed for the 1,5-diol motif. Fig. 1 Representative 1,5-diol structures.the generation of each stereocenter. Syntheses according to this strategy would confront challenging configurational assignments.In view of these concerns, new strategies and methods have begun to emerge in order to specifically address the 1,5-polyol problems, both in structural analysis and synthesis. The goal of this brief review is to highlight selected developments at the forefront of this new area. SELECTED NATURAL PRODUCTS WITH 1,5-POLYOL MOTIFSNatural products incorporating 1,5-diol and 1,5-polyol motifs exhibit a wide range of interesting structures and diverse biological activities. Tetrafibricin (1, Fig. 2), a fibrinogen receptor antagonist, was iso-G. K. FRIESTAD AND G. SREENILAYAM

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Section: Resultsmentioning

confidence: 99%

1,5-Polyols: Challenging motifs for configurational assignment and synthesis

Friestad

Sreenilayam

2011

Pure and Applied Chemistry

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“…This most recent example of silyl migration reaction is referred to as "anion relay chemistry". [77] It can certainly be stated that this field is far from being exhausted. In particular, catalytic reactions with acyl anion equivalents have recently seen a dramatic increase in interest.…”

Section: Discussionmentioning

confidence: 98%

Small and Versatile – Formyl Anion and Dianion Equivalents

et al. 2007

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This account provides a short overview of the synthetically important class of formyl anions and the less studied formyl dianion equivalents. A brief literature survey, which particularly focusses on asymmetric homologation strategies, is complemented by a detailed description of lithiated (dimethoxymethyl)diphenylphosphane oxide, which is an ideal formyl anion equivalent in reactions with aldehydes. Under acidic conditions the intermediate ketene O,O-acetals afford homologated carboxylic esters whereas asymmetric dihydroxylation of ketene acetals leads to collapse of the intermediate diols furnishing the corresponding α-hydroxy carboxylic esters with high stereocontrol. Additionally, it is demonstrated that the silyl-substituted carbanion may be looked

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“…4–6 Both the Brook rearrangement and the retro‐Brook rearrangement are currently widely applied in organic synthesis 1. 2 As illustrated in Scheme , a recent yet very useful strategy applying anionic migrations of silyl groups is the anion relay chemistry (ARC) developed by Smith III et al 7f,g,h,j,k. The ARC, a multi‐component linchpin protocol, has been demonstrated to be useful for high‐efficient and facile synthesis of structurally complex scaffolds 3.…”

Section: Methodsmentioning

confidence: 99%

Iterative Dianion Relay Along the Ring: Formation of gem‐Bis(trimethylsilyl) Cyclopentenones from 2,5‐Bis(trimethylsilyl) Oxy‐cyclopentadienyl Dianions and Acid Chlorides

Liu

Wang

et al. 2011

Chemistry A European J

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Sondenpaare mit Erkennungselementen entgegengesetzter Konfiguration können zur Detektion von Zielproteinen biologisch aktiver Naturstoffe verwendet werden. Die gezeigten, diastereomeren Sonden wurden auf Basis von Struktur‐Aktivitäts‐Beziehungen eines endogenen Faktors entworfen, der das Öffnen und Schließen der Blätter der Titelpflanze steuert. So wurde entdeckt, dass ein 38‐kDa‐Membranprotein der Schlüssel für die stereospezifische Erkennung des Naturstoffes ist.

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Anion Relay Chemistry: An Effective Tactic for Diversity Oriented Synthesis

Cited by 110 publications

References 13 publications

1,5-Polyols: Challenging motifs for configurational assignment and synthesis

1,5-Polyols: Challenging motifs for configurational assignment and synthesis

Small and Versatile – Formyl Anion and Dianion Equivalents

Iterative Dianion Relay Along the Ring: Formation of gem‐Bis(trimethylsilyl) Cyclopentenones from 2,5‐Bis(trimethylsilyl) Oxy‐cyclopentadienyl Dianions and Acid Chlorides

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