Efficient Asymmetric Synthesis of cis-4-Formyl .beta.-Lactams from L-(+)-Tartaric Acid

The Journal of Organic Chemistry ◽

10.1021/jo00083a042 ◽

1994 ◽

Vol 59 (4) ◽

pp. 932-934 ◽

Author(s):

M. Jayaraman ◽

A. R. A. S. Deshmukh ◽

B. M. Bhawal

Keyword(s):

Asymmetric Synthesis ◽

Tartaric Acid ◽

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Synthetic studies on optically active .BETA.-lactams. II. Asymmetric synthesis of .BETA.-lactams by (2+2)cyclocondensation using heterocyclic compounds derived from L-(+)-tartaric acid, (S)- or (R)-glutamic acid, and (S)-serine as chiral auxiliaries.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.38.1601 ◽

1990 ◽

Vol 38 (6) ◽

pp. 1601-1608 ◽

Author(s):

Nobuo IKOTA

Keyword(s):

Glutamic Acid ◽

Asymmetric Synthesis ◽

Tartaric Acid ◽

Heterocyclic Compounds ◽

Optically Active ◽

Chiral Auxiliaries ◽

Beta Lactams ◽

Synthetic Studies

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ChemInform Abstract: Asymmetric Synthesis of β-Lactams Using Chiral Five-Membered Heterocyclic Compounds Derived from (+)-Tartaric Acid and L-Amino Acids.

Chemischer Informationsdienst ◽

10.1002/chin.198439149 ◽

1984 ◽

Vol 15 (39) ◽

Author(s):

N. IKOTA ◽

A. HANAKI

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Tartaric Acid ◽

Heterocyclic Compounds

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ChemInform Abstract: Tartaric Acid, an Efficient Chiral Auxiliary: New Asymmetric Synthesis of 2-Alkyl-2-arylacetic Acids.

10.1002/chin.198751161 ◽

1987 ◽

Vol 18 (51) ◽

Author(s):

G. CASTALDI ◽

S. CAVICCHIOLI ◽

C. GIORDANO ◽

F. UGGERI

Keyword(s):

Asymmetric Synthesis ◽

Tartaric Acid ◽

Chiral Auxiliary ◽

Arylacetic Acids

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Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement

Australian Journal of Chemistry ◽

10.1071/ch09637 ◽

2010 ◽

Vol 63 (3) ◽

pp. 529 ◽

Author(s):

Leon S.-M. Wong ◽

Kathleen A. Turner ◽

Jonathan M. White ◽

Andrew B. Holmes ◽

John H. Ryan

Keyword(s):

Natural Products ◽

Asymmetric Synthesis ◽

Tartaric Acid ◽

Claisen Rearrangement ◽

Cyclic Carbonate ◽

Thermal Elimination ◽

Ketene Acetal ◽

The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.

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ChemInform Abstract: Efficient Asymmetric Synthesis of cis-4-Formyl β-Lactams from L-(+ )-Tartaric Acid.

10.1002/chin.199429147 ◽

2010 ◽

Vol 25 (29) ◽

pp. no-no

Author(s):

M. JAYARAMAN ◽

A. R. A. S. DESHMUKH ◽

B. M. BHAWAL

Keyword(s):

Asymmetric Synthesis ◽

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Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from l-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (−)-frontalin

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2006.07.007 ◽

2006 ◽

Vol 17 (13) ◽

pp. 1979-1984 ◽

Author(s):

Kavirayani R. Prasad ◽

Appayee Chandrakumar ◽

Pazhamalai Anbarasan

Keyword(s):

Asymmetric Synthesis ◽

Tartaric Acid ◽

Enantioselective Synthesis ◽

Insect Pheromone

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Asymmetric Synthesis of 1-(2- and 3-Haloalkyl)azetidin-2-ones as Precursors for Novel Piperazine, Morpholine, and 1,4-Diazepane Annulated Beta-Lactams

The Journal of Organic Chemistry ◽

10.1021/jo0608319 ◽

2006 ◽

Vol 71 (18) ◽

pp. 7083-7086 ◽

Author(s):

Willem Van Brabandt ◽

Matthieu Vanwalleghem ◽

Matthias D'hoogh ◽

Norbert De Kimpe

Keyword(s):

Asymmetric Synthesis ◽

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Asymmetric synthesis of .beta.-lactams and the carbapenem antibiotic (+)-PS-5

Journal of the American Chemical Society ◽

10.1021/ja00279a072 ◽

1986 ◽

Vol 108 (19) ◽

pp. 6054-6056 ◽

Author(s):

David J. Hart ◽

Chih Shone. Lee ◽

William H. Pirkle ◽

Myung Ho. Hyon ◽

Athanasios. Tsipouras

Keyword(s):

Asymmetric Synthesis ◽

Beta Lactams ◽

Carbapenem Antibiotic

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ChemInform Abstract: Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid.

10.1002/chin.199612254 ◽

2010 ◽

Vol 27 (12) ◽

pp. no-no

Author(s):

Y. S. LEE ◽

D. W. KANG ◽

S. J. LEE ◽

H. PARK

Keyword(s):

Asymmetric Synthesis ◽

Tartaric Acid ◽

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Asymmetric synthesis of .alpha.-alkyl-.alpha. amino acids from chromium-carbene-complex-derived .beta.-lactams

The Journal of Organic Chemistry ◽

10.1021/jo00074a016 ◽

1993 ◽

Vol 58 (22) ◽

pp. 5918-5924 ◽

Author(s):

Pierre Jean Colson ◽

Louis S. Hegedus

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Beta Lactams ◽

Carbene Complex ◽

Chromium Carbene

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