Short, stereoselective syntheses of 4,5,6-trihydroxylated norleucines: An approach to the synthesis of (+)-bulgecinine

Jackson, Richard F. W.; Rettie, Alan B.

doi:10.1016/s0040-4039(00)60500-2

Cited by 18 publications

(2 citation statements)

References 9 publications

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“…58 The utility of these reactions was exemplified by the short, stereoselective synthesis of protected 4,5,6-trihydroxylated norleucines via the protected 4-keto a-amino acid 30, which was reduced to the corresponding lactone 31 (Scheme 16). 59,60 The reaction was also performed with organozinc reagent ent-5b, prepared from D-serine, to give the C2 epimer of the intermediate 30 (in 45% yield), which offers a new synthetic approach to the synthesis of (+)-bulgecinine, the enantiomer of a component of the naturally occurring bulgecin glycopeptide. A recent paper reports the synthesis of a fragment of colchicine by the acylation of zinc reagent 5a (Scheme 17).…”

Section: Scheme 14mentioning

confidence: 99%

Development and Applications of Amino Acid Derived Organometallics

Rilatt¹,

Caggiano²,

Jackson³

2005

Synlett

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This Account describes the discovery and development of a family of organometallic reagents derived from naturally occurring a-amino acids that have found widespread use in the stereocontrolled synthesis of non-natural analogues of proteinogenic amino acids. The general approach that we have taken involves the conversion of the side chain of enantiomerically pure naturally occurring amino acids, such as serine, aspartic acid and glutamic acid, into the corresponding primary alkyl iodide, followed by conversion into the corresponding organozinc reagents. Subsequent palladium-or copper-catalysed reactions of these reagents allow the synthesis of a wide variety of functionalised a-, b-and g-amino acid derivatives, without loss of stereochemical integrity. Insights gained from spectroscopic and kinetic studies into the stability of functionalised organozinc reagents are included.

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Section: Scheme 14mentioning

confidence: 99%

Development and Applications of Amino Acid Derived Organometallics

Rilatt¹,

Caggiano²,

Jackson³

2005

Synlett

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“…Magnesium activated by association with aromatic compounds has been used to good effect in the preparation of other finely divided metals.y* The reaction of activated magnesium ('Reike' magnesium) with 1,3-dienes results in cycloaddition to magnesiumcontaining five-membered organometallics ( 1 13). Subsequent reaction with a n-C,-alkyl ( x = 3, dibromide gives spirocyclic products 1 14.93 4, dr 5) 113 114…”

Section: Magnesiummentioning

confidence: 99%

Main group organometallics in synthesis

Wills¹

1994

Contemp. Org. Synth.

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Stereoselective Amination of 5-Substituted γ-Lactones and γ-Lactams – A Convenient Route for the Preparation of 5-Substituted (3S,5S)-3-Acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-Acetylaminopyrrolidin-2-ones

Škof¹,

Svete²,

Kmetič³

et al. 1999

Eur. J. Org. Chem.

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5‐Substituted (S)‐tetrahydrofuran‐2‐ones (1a,b) and (S)‐pyrrolidin‐2‐ones (1c,d) were transformed in three steps, by treatment with tert‐butoxybis(dimethylamino)methane (Bredereck's reagent), followed by nitrosation and stereoselective catalytic hydrogenation, into the corresponding 5‐substituted (3S,5S)‐3‐acetylaminotetrahydrofuran‐2‐ones (4a,b) and (3S,5S)‐3‐acetylaminopyrrolidin‐2‐ones (4c,d).

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Short, stereoselective syntheses of 4,5,6-trihydroxylated norleucines: An approach to the synthesis of (+)-bulgecinine

Cited by 18 publications

References 9 publications

Development and Applications of Amino Acid Derived Organometallics

Development and Applications of Amino Acid Derived Organometallics

Main group organometallics in synthesis

Stereoselective Amination of 5-Substituted γ-Lactones and γ-Lactams – A Convenient Route for the Preparation of 5-Substituted (3S,5S)-3-Acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-Acetylaminopyrrolidin-2-ones

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