108
D. Enders, M.R.M. Hüttl, O. Niemeier
could be combined with an intramolecular Diels-Alder reaction in one
pot providing tricyclic carbon frameworks under control of five carboncarbon bonds and up to eight stereocenters. In addition N-heterocyclic
carbenes were successfully used in asymmetric benzoin reactions. The first asymmetric intramolecular crossed aldehyde-ketone benzoin reaction was developed yielding α-hydroxy tetralone and -indanone derivatives. This new principle could be extended to the asymmetric synthesis 3-hydroxy 4-chromanones demonstrating an efficient entry
to bioactive natural product synthesis possessing this structural motif.
The fast developing field of organocatalysis will yield new routes and
versatile synthetic methods, which can be applied in biomimetic processes.
References
Acevedo CM, Kogut EF, Lipton MA (2001) Synthesis and analysis of the sterically constrained l-glutamine analogues (3S,4R)-3,4-dimethyl-l-glutamine
and (3S,4R)-3,4-dimethyl-l-pyroglutamic acid. Tetrahedron 57:6353
Lehninger AL (1993) Principles of biochemistry. Worth, New York
Alexander C, Rietschel ET (1999) Bakterielle Lipopolysaccharide-Hochaktive
Stimulatoren der angeborenen Immunität. BIOspektrum (Heidelb) 4:275–
281
Angata T, Varki A (2002) Chemical diversity in the sialic acids and related
alpha-keto acids: an. evolutionary perspective. Chem Rev 102:439
Arduengo AJ 3rd (1999) Looking for stable carbenes: the difficulty in starting
anew. Acc Chem Res 32:913
Arduengo AJ 3rd, Harlow RL, Kline M (1991) A stable crystalline carbene.
J Am Chem Soc 113:361
Arduengo AJ 3rd, Dias HVR, Harlow RL, Kline M (1992) Electronic stabilization of nucleophilic carbenes. J Am Chem Soc 114:5530
Arduengo AJ 3rd, Kraftczyk R (1998) Auf der Suche nach Stabilen Carbenen.
R Chem Unserer Zeit 32:6
Arend M, Westermann B, Risch N (1998) Modern variants of the Mannich reaction. Angew Chem Int Ed Engl 37:1044–1070
Atsumi S, Umezawa K, Iinuma H, Naganawa H, Nakamura H, Iitaka Y,
Takeuchi T (1990a) Production, isolation and structure determination of
a novel beta-glucosidase inhibitor, cyclophellitol, from Phellinus sp. J Antibiot (Tokyo) 43:49–53
D. Enders, M.R.M. Hüttl, O. Niemeier
could be combined with an intramolecular Diels-Alder reaction in one
pot providing tricyclic carbon frameworks under control of five carboncarbon bonds and up to eight stereocenters. In addition N-heterocyclic
carbenes were successfully used in asymmetric benzoin reactions. The first asymmetric intramolecular crossed aldehyde-ketone benzoin reaction was developed yielding α-hydroxy tetralone and -indanone derivatives. This new principle could be extended to the asymmetric synthesis 3-hydroxy 4-chromanones demonstrating an efficient entry
to bioactive natural product synthesis possessing this structural motif.
The fast developing field of organocatalysis will yield new routes and
versatile synthetic methods, which can be applied in biomimetic processes.
References
Acevedo CM, Kogut EF, Lipton MA (2001) Synthesis and analysis of the sterically constrained l-glutamine analogues (3S,4R)-3,4-dimethyl-l-glutamine
and (3S,4R)-3,4-dimethyl-l-pyroglutamic acid. Tetrahedron 57:6353
Lehninger AL (1993) Principles of biochemistry. Worth, New York
Alexander C, Rietschel ET (1999) Bakterielle Lipopolysaccharide-Hochaktive
Stimulatoren der angeborenen Immunität. BIOspektrum (Heidelb) 4:275–
281
Angata T, Varki A (2002) Chemical diversity in the sialic acids and related
alpha-keto acids: an. evolutionary perspective. Chem Rev 102:439
Arduengo AJ 3rd (1999) Looking for stable carbenes: the difficulty in starting
anew. Acc Chem Res 32:913
Arduengo AJ 3rd, Harlow RL, Kline M (1991) A stable crystalline carbene.
J Am Chem Soc 113:361
Arduengo AJ 3rd, Dias HVR, Harlow RL, Kline M (1992) Electronic stabilization of nucleophilic carbenes. J Am Chem Soc 114:5530
Arduengo AJ 3rd, Kraftczyk R (1998) Auf der Suche nach Stabilen Carbenen.
R Chem Unserer Zeit 32:6
Arend M, Westermann B, Risch N (1998) Modern variants of the Mannich reaction. Angew Chem Int Ed Engl 37:1044–1070
Atsumi S, Umezawa K, Iinuma H, Naganawa H, Nakamura H, Iitaka Y,
Takeuchi T (1990a) Production, isolation and structure determination of
a novel beta-glucosidase inhibitor, cyclophellitol, from Phellinus sp. J Antibiot (Tokyo) 43:49–53