Synthesis, Inhaltsverzeichnis FEATUREARTICLE© Georg Thieme Verlag Stuttgart ˙ New YorkA Concise Synthesis of (2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol (LAB1)Puspesh K. Upadhyay, Pradeep Kumar*Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, IndiaFax: +91(2)25902629; e-Mail: pk.tripathi@ncl.res.in; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garner’s aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step. Key words Garner’s aldehyde - Wittig reaction - diastereoselectivity - alkaloid - azasugars - pyrrolidine Volltext Referenzen References <A NAME="RZ13110SS-1">1</A> Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1645 <A NAME="RZ13110SS-2">2</A> El Ashry ESH. Rashed N. Shobier AHS. Pharmazie 2000, 55: 331 <A NAME="RZ13110SS-3">3</A> El Nemr A. Tetrahedron 2000, 56: 8579 <A NAME="RZ13110SS-4A">4a</A> Coppola GM. Huster HF. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids Wiley; New York: 1987. <A NAME="RZ13110SS-4B">4b</A> Jurczak J. Golebiowski A. Chem. Rev. 1989, 89: 149 <A NAME="RZ13110SS-4C">4c</A> Golebiowski A. Jurczak J. Total Synthesis of Linocomycin and Related Chemistry, In Recent Progress in the Chemical Synthesis of Antibiotics Springer; Berlin: 1990. <A NAME="RZ13110SS-4D">4d</A> Reetz MT. Angew. Chem., Int. Ed. Engl. 1991, 30: 1531 <A NAME="RZ13110SS-4E">4e</A> Dondoni A. Carbohydrate Synthesis via Thiazoles, In Modern Synthetic Reactions Vol. 2: Scheffold R. Verlag Helvetica Chimica Acta; Basel: 1992. p.377 <A NAME="RZ13110SS-5">5</A> Jurczak J. Golebiowski A. The Synthesis of Antibiotic Amino Sugars from α-Amino Aldehydes, In Antibiotics and Antiviral Compounds, Chemical Synthesis and Modification Krohn K. Kirst H. Maag H. VCH; Weinheim: 1993. <A NAME="RZ13110SS-6">6</A> Jurczak J. Golebiowski A. From α-Amino Acids to Amino Sugars, In Studies in Natural Products Chemistry Vol. 4: . Elsevier; Amsterdam: 1989. <A NAME="RZ13110SS-7">7</A> Golebiowski A. Jurczak J. Synlett 1993, 241 <A NAME="RZ13110SS-8">8</A> Kiciak K. Jacobsson U. Golebiowski A. Jurczak J. Pol. J. Chem. 1993, 67: 685 <A NAME="RZ13110SS-9A">9a</A> Fleet GWJ. Witty DR. Tetrahedron: Asymmetry 1990, 1: 119 <A NAME="RZ13110SS-9B">9b</A> Hosaka A. Ichikawa S. Shindo H. Sato T. Bull. Chem. Soc. Jpn. 1989, 62: 797 <A NAME="RZ13110SS-9C">9c</A> Mulzer J. Becker R. Brunner E. J. Am. Chem. Soc. 1989, 111: 7500 <A NAME="RZ13110SS-9D">9d</A> Abiko A. Roberts JC. Takemasa T. Masamune S. Tetrahedron Lett. 1986, 27: 4536 <A NAME="RZ13110SS-9E">9e</A> Zanardi F. Battistini L. Nespi M. Rassu G. Spanu P. Cornia M. Casiraghi G. Tetrahedron: Asymmetry 1996, 7: 1167 <A NAME="RZ13110SS-9F">9f</A> Fleet GWJ. Son JC. Tetrahedron 1988, 44: 2637 <A NAME="RZ13110SS-9G">9g</A> Weir CA. Taylor CM. J. Org. Chem. 1999, 64: 1554 <A NAME="RZ13110SS-9H">9h</A> Chen SY. Joullie MM. Tetrahedron Lett. 1983, 24: 5027 <A NAME="RZ13110SS-9I">9i</A> Bols M. Lundt I. Acta Chem. Scand. 1992, 46: 298 <A NAME="RZ13110SS-9J">9j</A> Kim HJ. Lee WS. Yang MS. Lee SG. Park KH. Synlett 1999, 614 <A NAME="RZ13110SS-9K">9k</A> Kim IS. Zee OP. Jung YH. Org. Lett. 2006, 8: 4101 <A NAME="RZ13110SS-10A">10a</A> Karl J.-U. Wieland T. Liebigs Ann. Chem. 1981, 1445 <A NAME="RZ13110SS-10B">10b</A> Durand J.-O. Larchevêque M. Petit Y. Tetrahedron Lett. 1998, 39: 5743 <A NAME="RZ13110SS-10C">10c</A> Arakawa Y. Yoshifuji S. Chem. Pharm. Bull. 1991, 39: 2219 <A NAME="RZ13110SS-10D">10d</A> Humphrey AJ. Parsons SF. Smith MEB. Turner NJ. Tetrahedron Lett. 2000, 41: 4481 <A NAME="RZ13110SS-10E">10e</A> Hulme AN. Montgomery CH. Henderson DK. J. Chem. Soc., Perkin Trans. 1 2000, 1837 <A NAME="RZ13110SS-10F">10f</A> Huwe CM. Blechert S. Synthesis 1997, 61 <A NAME="RZ13110SS-10G">10g</A> Goli DM. Cheesman BV. Hassan ME. Lodaya R. Slama JT. Carbohydr. Res. 1994, 259: 219 <A NAME="RZ13110SS-10H">10h</A> Ribes C. Falomir E. Carda M. Marco JA. J. Org. Chem. 2008, 73: 7779 ; and references cited therein <A NAME="RZ13110SS-11A">11a</A> Jones DWC. Nash RJ. Bell EA. Williams JM. Tetrahedron Lett. 1985, 26: 3125 <A NAME="RZ13110SS-11B">11b</A> Dhavale DD. Kumar KSA. Chaudhari VD. Sharma T. Sabharwal SG. Reddy JP. Org. Biomol. Chem. 2005, 3: 3720 <A NAME="RZ13110SS-11C">11c</A> Sugiyama M. Hong Z. Liang P.-H. Dean SM. Whalen LJ. Greenberg WA. Wong C.-H. J. Am. Chem. Soc. 2007, 129: 14811 <A NAME="RZ13110SS-11D">11d</A> Huang Y. Dalton DR. J. Org. Chem. 1997, 62: 372 <A NAME="RZ13110SS-11E">11e</A> Zhou X. Liu W.-H. Ye J.-L. Huang P.-Q. Tetrahedron 2007, 63: 6364 <A NAME="RZ13110SS-11F">11f</A> Lombardo M. Fabbroni S. Trombini C. J. Org. Chem. 2001, 66: 1264 <A NAME="RZ13110SS-12A">12a</A> Pandey SK. Kumar P. Synlett 2007, 2894 <A NAME="RZ13110SS-12B">12b</A> Pandey SK. Kumar P. Tetrahedron Lett. 2005, 46: 4091 <A NAME="RZ13110SS-12C">12c</A> Cherian SK. Kumar P. Tetrahedron: Asymmetry 2007, 18: 982 <A NAME="RZ13110SS-12D">12d</A> Kandula SV. Kumar P. Tetrahedron 2006, 62: 9942 <A NAME="RZ13110SS-12E">12e</A> Kumar P. Bodas MS. J. Org. Chem. 2005, 70: 360 <A NAME="RZ13110SS-12F">12f</A> Bodas MS. Upadhyay PK. Kumar P. Tetrahedron Lett. 2004, 45: 987 <A NAME="RZ13110SS-12G">12g</A> Upadhyay PK. Prasad R. Pandey M. Kumar P. Tetrahedron Lett. 2009, 50: 2440 <A NAME="RZ13110SS-13A">13a</A> Garner P. Park JM. J. Org. Chem. 1987, 52: 2361 <A NAME="RZ13110SS-13B">13b</A> Garner P. Park JM. Org. Synth. 1991, 70: 18 <A NAME="RZ13110SS-13C">13c</A> Garner P. Ramakanth S. J. Org. Chem. 1986, 51: 2609 <A NAME="RZ13110SS-13D">13d</A> Garner P. Park JM. Mallecki E. J. Org. Chem. 1988, 53: 4395 <A NAME="RZ13110SS-14A">14a</A> Kolb HC. VanNiewenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483 <A NAME="RZ13110SS-14B">14b</A> Becker H. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996, 35: 448 <A NAME="RZ13110SS-15">15</A> Dondoni A. Merino P. Perrone D. Tetrahedron 1993, 49: 2939