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

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.

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

References

<A NAME="RC12704SS-1">1</A>

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

<A NAME="RC12704SS-2">2</A>

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

<A NAME="RC12704SS-3">3</A>

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

<A NAME="RC12704SS-4">4</A> Clamp A. Jayson GC. Anti-Cancer Drugs  2002,  13:  673 

<A NAME="RC12704SS-5">5</A> Pettit GR. Herald CL. Doubek DL. Herald DL. Arnold E. Clardy J. J. Am. Chem. Soc.  1982,  104:  6846 

<A NAME="RC12704SS-6">6</A> For a survey see: Hale KJ. Hummersone MG. Manaviazar S. Frigerio M. Nat. Prod. Rep.  2002,  19:  413 

<A NAME="RC12704SS-7">7</A> 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 

<A NAME="RC12704SS-8A">8a</A> 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 

<A NAME="RC12704SS-8B">8b</A> Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev.  1994,  94:  2483 

<A NAME="RC12704SS-9A">9a</A> Ohmori K. Suzuki T. Nishiyama S. Yamamura S. Tetrahedron Lett.  1995,  36:  6515 

<A NAME="RC12704SS-9B">9b</A> Masamune S. Pure Appl. Chem.  1988,  60:  1587 

<A NAME="RC12704SS-9C">9c</A> Roy R. Rey AW. Charron M. Molino R. J. Chem. Soc., Chem. Commun.  1989,  1308 

<A NAME="RC12704SS-10">10</A> Evans DA. Carter PH. Carreira EM. Charette AB. Prunet JA. Lautens M. J. Am. Chem. Soc.  1999,  121:  7540 

<A NAME="RC12704SS-11">11</A> Hale KJ. Lennon JA. Manaviazar S. Javaid MH. Tetrahedron Lett.  1995,  36:  1359 

<A NAME="RC12704SS-12">12</A> 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 

<A NAME="RC12704SS-13A">13a</A> Markó IE. Svendsen JE. In Comprehensive Asymmetric Catalysis   Vol. II:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  p.713-787  

<A NAME="RC12704SS-13B">13b</A> Bolm C. Hildebrand JP. Muñiz K. In Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000.  p.399-428  

<A NAME="RC12704SS-13C">13c</A> Beller M. Sharpless KB. In Applied Homogeneous Catalysis with Organometallic Compounds   2nd ed.:  Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 2002.  p.1149-1164  

<A NAME="RC12704SS-13D">13d</A>

See also ref. 8b

<A NAME="RC12704SS-14">14</A> Carreira EM. Du Bois J. J. Am. Chem. Soc.  1994,  116:  10825 

<A NAME="RC12704SS-15">15</A> 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 

<A NAME="RC12704SS-16">16</A> Liang J. Moher ED. Moore RE. Hoard DW. J. Org. Chem.  2000,  65:  3143 

<A NAME="RC12704SS-17">17</A>

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

<A NAME="RC12704SS-18">18</A>

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

<A NAME="RC12704SS-19">19</A> Crispino GA. Jeong K.-S. Kolb HC. Wang Z.-M. Xu D. Sharpless KB. J. Org. Chem.  1993,  58:  3785 

<A NAME="RC12704SS-20A">20a</A> Moitessier N. Maigret B. Chrétien F. Chapleur Y. Eur. J. Org. Chem.  2000,  995 

<A NAME="RC12704SS-20B">20b</A> Andrus MB. Shih T.-Z. J. Org. Chem.  1996,  61:  8780 

<A NAME="RC12704SS-20C">20c</A>

See also ref. 15

<A NAME="RC12704SS-21">21</A> Becker H. Sharpless KB. Angew. Chem.  1996,  108:  447 

For synthetic applications of dihydroxylation reactions of terminal double bonds using the AQN-ligand see:

<A NAME="RC12704SS-22A">22a</A> Denmark SE. Martinsborough EA. J. Am. Chem. Soc.  1999,  121:  3046 

<A NAME="RC12704SS-22B">22b</A> Burke SD. Jiang L. Org. Lett.  2001,  3:  1953 

<A NAME="RC12704SS-22C">22c</A>

See also ref. 13.

<A NAME="RC12704SS-23A">23a</A> Corey EJ. Noe MC. Grogan MJ. Tetrahedron Lett.  1994,  35:  6427 

<A NAME="RC12704SS-23B">23b</A> Corey EJ. Noe MC. Ting AY. Tetrahedron Lett.  1996,  37:  1735 

<A NAME="RC12704SS-24">24</A> Corey EJ. Zhang J. Org. Lett.  2001,  3:  3211 

<A NAME="RC12704SS-25A">25a</A> Schrake O. Braje WM. Hoffmann HMR. Wartchow R. Tetrahedron: Asymmetry  1998,  9:  3717 

<A NAME="RC12704SS-25B">25b</A> Wartchow R. Schrake O. Braje WM. Hoffmann HMR. Z. Kristallogr. NCS  1999,  214:  285 

<A NAME="RC12704SS-25C">25c</A> Wartchow R. Frackenpohl J. Hoffmann HMR. Z. Kristallogr. NCS  2001,  216:  235 

<A NAME="RC12704SS-25D">25d</A> Braje WM. Frackenpohl J. Schrake O. Wartchow R. Beil W. Hoffmann HMR. Helv. Chim. Acta  2000,  83:  777 

<A NAME="RC12704SS-26">26</A> Frackenpohl J. Braje W. Hoffmann HMR. J. Chem. Soc., Perkin Trans. 1  2001,  47 

<A NAME="RC12704SS-27">27</A>

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.