Stereoselective syntheses of (.+-.)-daunosamine, (.+-.)-vancosamine, and (.+-.)-ristosamine from acyclic precursors

Hauser, Frank M.; Ellenberger, Suzanne R.; Glusker, Jenny P.; Smart, C. J.; Carrell, H. L.

doi:10.1021/jo00351a009

Cited by 48 publications

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“…After cleavage of the chiral auxiliary using 15% citric acid the amino ester 15a was obtained in 50% yield. Epoxides are versatile intermediates 14 in organic synthesis and a large variety of reagents are known for the ring opening of these compounds; 14a and (or) 15a represent interesting precursors for the synthesis of diversely β-substituted β-hydroxy aspartic acid derivatives.…”

Section: Resultsmentioning

confidence: 99%

Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

et al. 2003

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Section: Resultsmentioning

confidence: 99%

Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

et al. 2003

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“…The furan moiety could arise from a palladium‐catalyzed, Wacker‐type cyclization. Diol 5 should be accessible from the cyclohexenone 6 , which would in turn be available through our proline‐sulfonamide catalyzed protocol using known aldehyde 7 and enone 8 …”

Section: Figurementioning

confidence: 99%

Enantioselective Synthesis of (−)‐Halenaquinone

et al. 2018

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The efficient, 12-14 step (LLS) total synthesis of (À)-halenaquinone has been achieved. Keys teps in the synthetic sequence include:(a) proline sulfonamide-catalyzed, Yamada-Otani reaction to establish the C6 all-carbon quaternary stereocenter,( b) multiple,n ovel palladium-mediated oxidative cyclizations to introduce the furan moiety,a nd (c) oxidative Bergman cyclization to form the final quinone ring.

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“…Although this rearrangement has found use in organic synthesis (for example see [29] and [48]), the more common variant, the [ imidates is especially widespread (Scheme 23). In particular, the rearrangement of allylic trichloroacetimidates, commonly known as the Overman rearrangement has been employed as the key step in the synthesis of a variety of nitrogen containing molecules including alkaloids, antibiotics, unnatural amino acids and drug-like molecules [35,[49][50][51][52][53][54][55][56][57][58].…”

Section: Palladium(ii)-catalysed Aza-claisen Rearrangementsmentioning

confidence: 99%

Palladium(II)-Catalysed Rearrangement Reactions

Fanning¹,

Jamieson²,

Sutherland³

2006

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The synthesis of new carbon-carbon and carbon-heteroatom bonds in a stereochemically well defined manner still presents a challenge in modern synthetic methodology. An important class of reactions, which can carry out the aforementioned transformations, are the [3,3]-sigmatropic rearrangements. These rearrangements have traditionally been carried out thermally at high temperatures. However, the discovery that these transformations can be accelerated by Pd(II) at ambient temperature has led to more widespread use of these reactions for the synthesis of biologically active and pharmaceutically important molecules.This review presents an overview of the use of palladium(II) catalysis for the acceleration of three of the most commonly used rearrangements in organic chemistry, namely, the Cope, Claisen and aza-Claisen rearrangements. In particular, the mechanism of catalysis, stereochemical outcome and synthetic application of these reactions will be discussed.

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Stereoselective syntheses of (.+-.)-daunosamine, (.+-.)-vancosamine, and (.+-.)-ristosamine from acyclic precursors

Cited by 48 publications

References 0 publications

Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

Enantioselective Synthesis of (−)‐Halenaquinone

Palladium(II)-Catalysed Rearrangement Reactions

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