Chemoenzymatic Carbon-Carbon Bond Formation Leading to Non-carbohydrate Derivative. Stereoselective Synthesis of Pentamycin C-11-C-16 Fragment.

Shimagaki, Masayuki; Muneshima, Hiroaki; Kubota, Masahide; Oishi, Takeshi

doi:10.1248/cpb.41.282

Cited by 16 publications

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“…171 In der Totalsynthese des Antibiotikums Pentamycin ( 248 ) wurde das C9‐C16‐Teilstück durch eine FruA‐katalysierte Aldoladdition von DHAP (Dihydroxyacetonphosphat) mit dem chiralen Aldehyd 249 erhalten (FruA= D ‐Fructose‐1,6‐bisphosphataldolase; Schema 48) 172. 173…”

Section: Enzymkatalysierte Aldolreaktionenunclassified

Aldolreaktionen in der Totalsynthese von Polyketiden

Schetter

Mahrwald

2006

Angewandte Chemie

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Die Aldolreaktion gehört zu den wichtigsten Methoden der organischen Synthesechemie für den stereoselektiven Aufbau von polyketiden Naturstoffen. Dabei bedient sich die Natur gleichermaßen wie der präparativ arbeitende Chemiker dieser fundamentalen Reaktion. Die rasante Entwicklung auf dem Gebiet der stereoselektiven Aldolreaktionen während der letzten 30 Jahre führte zur Totalsynthese vieler komplexer Naturstoffe. Dieser Beitrag illustriert anhand ausgewählter Totalsynthesen von Naturstoffen diese neuartigen Varianten der Aldoladdition. Dabei werden Aldoladditionen, die sich unterschiedlicher Metallenolate bedienen, ebenso behandelt wie metallkomplexkatalysierte, organokatalytische sowie biokatalytische Methoden.

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Section: Enzymkatalysierte Aldolreaktionenunclassified

Aldolreaktionen in der Totalsynthese von Polyketiden

Schetter

Mahrwald

2006

Angewandte Chemie

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Aldol Reaction – Biological and Biomimetic

Dickerson

Córdova

Chen

et al. 2002

Encyclopedia of Catalysis

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In order to develop new methodology for stereospecific and catalytic aldol reactions, synthetic organic chemists are now exploring the utility of biological catalysts. There has been significant progress in this field and several efficient, selective, and predictable biological catalysts are now available for the asymmetric aldol reaction. Critical to metabolism, the aldolases catalyze in vivo aldol reactions with high chemo‐, regio‐, diastereo‐, and enantioselectivity. These enzymes are divided into four distinct areas: DHAP‐dependent, pyruvate/phosphoenol pyruvate‐dependent, acetaldehyde‐dependent, and glycine‐dependent aldolases based upon their donor dependence. Catalytic antibodies that operate via a mechanism reminiscent of a type I aldolase also have been developed. These antibodies have remarkable rate accelerations and broader substrate specificity compared to naturally occurring aldolases. However, both aldolases and catalytic antibodies share a common feature critical to their success as synthetically useful catalysts—both are capable of tolerating substrates with unprotected functional groups in aqueous solutions and give readily predictable products. This article will focus on the development of these two areas of biological aldol catalysts and discuss relevant examples as appropriate.

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Enzyme‐catalyzed Aldol Additions

Fessner¹

2004

Modern Aldol Reactions

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Chemoenzymatic Carbon-Carbon Bond Formation Leading to Non-carbohydrate Derivative. Stereoselective Synthesis of Pentamycin C-11-C-16 Fragment.

Cited by 16 publications

References 0 publications

Aldolreaktionen in der Totalsynthese von Polyketiden

Aldolreaktionen in der Totalsynthese von Polyketiden

Aldol Reaction – Biological and Biomimetic

Enzyme‐catalyzed Aldol Additions

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