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Synthesis 2004(9): 1391-1398  
DOI: 10.1055/s-2004-822400
PAPER
© Georg Thieme Verlag Stuttgart · New York

Studies on the Asymmetric Dihydroxylation of Advanced Bryostatin C-Ring Segments

Martin C. Seidel, René Smits, Christian B. W. Stark, Jens Frackenpohl, Oliver Gaertzen, H. Martin R. Hoffmann*
Department of Organic Chemistry, University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Fax: +49(511)7623011; e-Mail: hoffmann@mbox.oci.uni-hannover.de;
Further Information

Publication History

Received 15 April 2004
Publication Date:
08 June 2004 (online)

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Abstract

The asymmetric dihydroxylation reaction of early stage and advanced Bryostatin C-ring precursors was evaluated. For homoallylic ethers and alcohols, several AD ligands were investigated including a novel class of quinidine-alkynes.

Key words

asymmetric dihydroxylation - Bryostatin - quinidine-based ligands - double stereoinduction - Cinchona alkynes

    References

  • 4 Clamp A. Jayson GC. Anti-Cancer Drugs  2002,  13:  673 
    CrossrefGoogle Scholar
  • 5 Pettit GR. Herald CL. Doubek DL. Herald DL. Arnold E. Clardy J. J. Am. Chem. Soc.  1982,  104:  6846 
    CrossrefGoogle Scholar
  • 6 For a survey see: Hale KJ. Hummersone MG. Manaviazar S. Frigerio M. Nat. Prod. Rep.  2002,  19:  413 
    CrossrefGoogle Scholar
  • 7 Wender PA. DeBrabander J. Harran PG. Jimenez J.-M. Koehler MFT. Lippa B. Park C.-M. Siedenbiedel C. Pettit GR. Proc. Natl. Acad. Sci. U.S.A.  1998,  95:  6624 
    CrossrefGoogle Scholar
  • 8a Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D. Zhang X.-L. J. Org. Chem.  1992,  57:  2768 
    Google Scholar
  • 8b Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev.  1994,  94:  2483 
    Google Scholar
  • 9a Ohmori K. Suzuki T. Nishiyama S. Yamamura S. Tetrahedron Lett.  1995,  36:  6515 
    CrossrefGoogle Scholar
  • 9b Masamune S. Pure Appl. Chem.  1988,  60:  1587 
    CrossrefGoogle Scholar
  • 9c Roy R. Rey AW. Charron M. Molino R. J. Chem. Soc., Chem. Commun.  1989,  1308 
    CrossrefGoogle Scholar
  • 10 Evans DA. Carter PH. Carreira EM. Charette AB. Prunet JA. Lautens M. J. Am. Chem. Soc.  1999,  121:  7540 
    CrossrefGoogle Scholar
  • 11 Hale KJ. Lennon JA. Manaviazar S. Javaid MH. Tetrahedron Lett.  1995,  36:  1359 
    CrossrefGoogle Scholar
  • 12 Wender PA. Baryza JL. Bennett CE. Bi FC. Brenner SE. Clarke MO. Horan JC. Kan C. Lacote E. Lippa B. Nell PG. Turner TM. J. Am. Chem. Soc.  2002,  124:  13648 
    CrossrefPubMedGoogle Scholar
  • 13a Markó IE. Svendsen JE. In Comprehensive Asymmetric Catalysis   Vol. II:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  p.713-787  
    Google Scholar
  • 13b Bolm C. Hildebrand JP. Muñiz K. In Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000.  p.399-428  
    Google Scholar
  • 13c Beller M. Sharpless KB. In Applied Homogeneous Catalysis with Organometallic Compounds   2nd ed.:  Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 2002.  p.1149-1164  
    Google Scholar
  • 13d

    See also ref. 8b

  • 14 Carreira EM. Du Bois J. J. Am. Chem. Soc.  1994,  116:  10825 
    CrossrefGoogle Scholar
  • 15 Nicolaou KC. Li Y. Sugita K. Monenschein H. Guntupalli P. Mitchell HJ. Fylaktakidou KC. Vourloumis D. Giannakakou P. O’Brate A. J. Am. Chem. Soc.  2003,  125:  15443 
    CrossrefGoogle Scholar
  • 16 Liang J. Moher ED. Moore RE. Hoard DW. J. Org. Chem.  2000,  65:  3143 
    CrossrefGoogle Scholar
  • 19 Crispino GA. Jeong K.-S. Kolb HC. Wang Z.-M. Xu D. Sharpless KB. J. Org. Chem.  1993,  58:  3785 
    CrossrefGoogle Scholar
  • 20a Moitessier N. Maigret B. Chrétien F. Chapleur Y. Eur. J. Org. Chem.  2000,  995 
    CrossrefPubMedGoogle Scholar
  • 20b Andrus MB. Shih T.-Z. J. Org. Chem.  1996,  61:  8780 
    CrossrefPubMedGoogle Scholar
  • 20c

    See also ref. 15
    CrossrefPubMed
  • 21 Becker H. Sharpless KB. Angew. Chem.  1996,  108:  447 
    Google Scholar
  • For synthetic applications of dihydroxylation reactions of terminal double bonds using the AQN-ligand see:
  • 22a Denmark SE. Martinsborough EA. J. Am. Chem. Soc.  1999,  121:  3046 
    CrossrefGoogle Scholar
  • 22b Burke SD. Jiang L. Org. Lett.  2001,  3:  1953 
    CrossrefGoogle Scholar
  • 22c

    See also ref. 13.
    CrossrefGoogle Scholar
  • 23a Corey EJ. Noe MC. Grogan MJ. Tetrahedron Lett.  1994,  35:  6427 
    CrossrefGoogle Scholar
  • 23b Corey EJ. Noe MC. Ting AY. Tetrahedron Lett.  1996,  37:  1735 
    CrossrefGoogle Scholar
  • 24 Corey EJ. Zhang J. Org. Lett.  2001,  3:  3211 
    CrossrefPubMedGoogle Scholar
  • 25a Schrake O. Braje WM. Hoffmann HMR. Wartchow R. Tetrahedron: Asymmetry  1998,  9:  3717 
    CrossrefGoogle Scholar
  • 25b Wartchow R. Schrake O. Braje WM. Hoffmann HMR. Z. Kristallogr. NCS  1999,  214:  285 
    CrossrefGoogle Scholar
  • 25c Wartchow R. Frackenpohl J. Hoffmann HMR. Z. Kristallogr. NCS  2001,  216:  235 
    CrossrefGoogle Scholar
  • 25d Braje WM. Frackenpohl J. Schrake O. Wartchow R. Beil W. Hoffmann HMR. Helv. Chim. Acta  2000,  83:  777 
    CrossrefGoogle Scholar
  • 26 Frackenpohl J. Braje W. Hoffmann HMR. J. Chem. Soc., Perkin Trans. 1  2001,  47 
    CrossrefGoogle Scholar
1

New address: Christian B. W. Stark, Department of Organic Chemistry, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.

2

New address: J. Frackenpohl, Bayer CropScience GmbH, Chemistry Frankfurt, G836, Industriepark Höchst, 65926 Frankfurt am Main, Germany.

3

New address: Oliver Gaertzen, Bayer CropScience AG, Alfred Nobel Str. 50, 40789 Monheim, Germany.

17

To determine the ratio of diastereoselectivity for the dihydroxylated lactol of 1 the diol was first transformed into the corresponding acetonide, followed by oxidation to lactone 11 (Equation [3] ).

Equation 3

18

The synthesis of these fragments will be presented in due course.

27

Although complete conversion was noted in these experiments, the yield of isolated product was generally low when structurally complex substrates were converted. Thus far, no degradation products could be isolated, implying the formation of highly water-soluble side-products.