A Flexible Approach to Protected (4S,5S)-5-Alkyl-1-benzyl-4-benzyloxy-2-pyrrolidinones

REFERENCES

• For reviews on the occurrence, biological properties, and syntheses of pyrrolidines, see (a) Numata , A. ; Ibuka , T. In The Alkaloids ; A. Brossi , (Ed.); Academic Press : New York , 1987 ; vol. 31 , Chapter 6; (b) Hartmann , T. ; Witte , L. In Alkaloids: Chemical and Biological Perspectives ; S. W. Pelletier , (Ed.); Elsevier Science : New York , 1995 ; vol. 9 , chapter 4; (c) O'Hagan, D. Pyrrole, pyrrolidine, pyridine, piperidine, azepine and tropane alkaloids. Nat. Prod. Rep. 1997, 14, 637–651; (d) Liddell, J. M. Pyrrolizidine alkaloids. Nat. Prod. Rep. 1999, 16, 499–507; (e) Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Polyhydroxylated alkaloids—natural occurrence and therapeutic applications. Phytochemistry 2001, 56, 265–295; (f) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Sugar-mimic glycosidase inhibitors: Natural occurrence, biological activity, and prospects for therapeutic application. Tetrahedron: Asymmetry 2000, 11, 1645–1680.
   Google Scholar
• (a) Provencher , L. ; Steensma , D. H. ; Wong , C. H. Five-membered ring azasugars as potent inhibitors of α-L-rhamnosidase (naringinase) from Penicillium decumbens . Bioorg. Med. Chem. 1994 , 2 , 1179 – 1188 ; (b) Joubert , M. ; Defoin , A. ; Tarnus , C. ; Streith , J. Synthesis of potent α-d-mannosidase and α-l-fucosidase inhibitors: 4-Amino-4-deoxy-d-erythrose and 4-amino-4,5-dideoxy-l-lyxose . Synlett 2000 , 1366 – 1368 .
   PubMedGoogle Scholar
• Sobin , B. A. ; Tanner Jr. , F. W. Anisomycin, a new anti-protozoan antibiotic . J. Am. Chem. Soc. 1954 , 76 , 4053 .
   Web of Science ®Google Scholar
• (a) Jimenez , A. ; Vazquez , D. Anisomycin and related antibiotics . In Antibiotics ; F. E. Hahn (Ed.), Springer Verlag ; Berlin , 1979 ; pp. 1 – 19 . For recent examples, see (b) Inverarity, I. A.; Hulme, A. N. Marked small molecule libraries: A truncated approach to molecular probe design. Org. Biomol. Chem. 2007, 5, 636–643.
   Google Scholar
• (a) Denmark , S. E. ; Parker Jr. , D. L. ; Dixon , J. A. Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes, 12: Synthesis of (−)-platynecine. J. Org. Chem. 1997, 62, 435–436; (b) Kang , S. H. ; Kim , G. T. ; Yoo , Y. S. An enantiocontrolled synthesis of pyrrolizidines, (−)-platynecine and (−)-hadinecine. Tetrahedron Lett. 1997, 38, 603–606; (c) Hashimura , K. ; Tomita , S. ; Hiroya , K. ; Ogasawara , K. A stereocontrolled route to both enantiomers of the necine base dihydroxyheliotridane via intramolecular 1,3-dipolar addition using the same chiral precursor. J. Chem. Soc. Chem. Commun. 1995, 2291–2292.
   PubMed Web of Science ®Google Scholar
• For selected examples, see (a) Diez , D. ; Beneitez , M. T. ; Marcos , I. S. ; Garrido , N. M. ; Basabe , P. ; Urones , J. G. Regio- and stereoselective ring opening of epoxides: Enantioselective synthesis of 2,3,4-trisubstituted five-membered heterocycles . Tetrahedron: Asymmetry 2002 , 13 , 639 – 646 ; (b) Chevrier , C. ; LeNouen , D. ; Neuburger , M. ; Defoina , A. ; Tarnusa , C. Nitrone in L-lyxose series: Cycloaddition way for the synthesis of new C-α-fucosides . Tetrahedron Lett. 2004 , 45 , 5363 – 5366 .
   Web of Science ®Google Scholar
• Huang , P. Q. ; Wang , S. L. ; Ye , J. L. ; Ruan , Y. P. ; Huang , Y. Q. ; Zheng , H. ; Gao , J. X. An easy access to protected (4S,5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates . Tetrahedron 1998 , 54 , 12547 – 12560 .
   Web of Science ®Google Scholar
• For two accounts, see (a) Huang , P. Q. Asymmetric synthesis of hydroxylated pyrrolidines, piperidines, and related bioactive compounds: From N-acyliminium chemistry to N-α-carbanion chemistry . Synlett 2006 , 1133 – 1149 ; (b) Huang, P. Q. Recent advances on the asymmetric synthesis of bioactive 2-pyrrolidinone-related compounds starting from enantiomeric malic acid, in new methods for the asymmetric synthesis of nitrogen heterocycles. In New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles; J. L. Vicario, D. Badia, and L. Carillo (Eds.); Research Signpost: Kerala, 2005; pp. 197–222.
   Web of Science ®Google Scholar
• Xiang , S.-H. ; Yuan , H.-Q. ; Huang , P.-Q. A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: Asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine . Tetrahedron: Asymmetry 2009 , 20 , 2020 – 2026 .
   Web of Science ®Google Scholar
• For reviews on the use of Zn(BH4)2, see (a) Oishi , T. ; Nakata , T. An introduction of chiral centers into acyclic systems based on stereoselective ketone reduction . Acc. Chem. Res. 1984 , 17 , 338 – 344 ; (b) Ranu , B. C. Zinc borohydride, a reducing agent with high potential . Synlett 1993 , 885 – 892 ; (c) Narasimhan , S. ; Balakumar , R. Synthetic applications of zinc borohydride . Aldrichim. Acta 1998 , 31 , 19 – 26 .
   Web of Science ®Google Scholar
• (a) Luo , F.-T. ; Jeevanandam , A. Simple transformation of nitrile into ester by the use of chlorotrimethylsilane . Tetrahedron Lett. 1998 , 39 , 9455 – 9456 ; (b) Baskaran , S. ; Chidambaram , N. ; Narasimhan , N. ; Chandrasekaran , S. A novel and unusual reaction of enol ethers with banzyltriethylammonium borohydride and chlorotrimethylsilane . Tetrahedron Lett. 1992 , 33 , 6371 – 6374 ; (c) Afonso , C. A. M. ; Motherwell , W. B. ; Roberts , L. R. Observations on the selective deoxygenation of epoxides to olefins with chlorotrimethylsilane and zinc . Tetrahedron Lett. 1992 , 33 , 3367 – 3370 ; (d) Kosarych , Z. ; Cohen , T. Rapid, high-yield cleavage of enol and dienol methyl ethers under mild conditions using chlorotrimethylsilane/sodium iodide . Tetrahedron Lett. 1980 , 21 , 3959 – 3962 .
   Web of Science ®Google Scholar
• (a) Alinezhad , H. ; Tajbakhsh , M. ; Salehian , F. ; Fazli , K. Reductive amination of aldehydes and ketones to their corresponding amines with N-methylpyrrolidine zinc borohydride . Tetrahedron Lett. 2009 , 50 , 659 – 661 ; (b) Kotsuki , H. ; Ushio , Y. ; Yoshimura , N. ; Ochi , M. Efficient method for the reductive cleavage of acetals and ketals with Zn(BH4)/Me3SiC1 . J. Org. Chem. 1987 , 52 , 2594 – 2596 .
   Web of Science ®Google Scholar
• Liu , L.-X. ; Xiao , K.-J. ; Huang , P.-Q. Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones . Tetrahedron 2009 , 65 , 3834 – 3841 .
   Web of Science ®Google Scholar
• Bernardi , A. ; Micheli , F. ; Potenza , D. ; Scolastico , C. ; Villa , R. Stereoselective synthesis of statin analogues . Tetrahedron Lett. 1990 , 31 , 4949 – 4952 .
   Web of Science ®Google Scholar
• Ye , J.-L. , Huang , P.-Q. , Lu , X. Mechanism for the regioselective asymmetric addition of Grignard reagents to malimides: A computational exploration . J. Org. Chem. 2007 , 72 , 35 – 42 .
   PubMed Web of Science ®Google Scholar