Synthesis of the C1-C13
Subunit of Spirastrellolides A and B by Prins Cyclization

Gowravaram Sabitha; A. Senkara Rao; Jhillu S. Yadav

doi:10.1055/s-0029-1218588

PAPER

Synthesis of the C1-C13 Subunit of Spirastrellolides A and B by Prins Cyclization

Gowravaram Sabitha*, A. Senkara Rao, Jhillu S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com;

Abstract

Alle Artikel dieser Rubrik

Abstract

The C1-C13 subunit of the marine natural products spirastrellolides A and B, which contains a cis-substituted tetrahydropyran ring, was prepared by using the Prins cyclization strategy.

Key words

tetrahydropyrans - diastereoselectivity - homoallylic alcohols - aldehydes - cyclizations

Volltext

Referenzen

References

<A NAME="RZ17809SS-1A">1a</A> Blunt JW. Copp BR. Munro MHG. Northcote PT. Prinsep MR. Nat. Prod. Rep. 2005, 22: 15

<A NAME="RZ17809SS-1B">1b</A> Newman DJ. Cragg GM. J. Nat. Prod. 2004, 67: 1216

<A NAME="RZ17809SS-1C">1c</A> Yeung K.-S. Paterson I. Chem. Rev. 2005, 105: 4237

<A NAME="RZ17809SS-2A">2a</A> Williams DE. Roberge M. Van Soest R. Andersen RJ. J. Am. Chem. Soc. 2003, 125: 5296

<A NAME="RZ17809SS-2B">2b</A> Williams DE. Roberge M. Andersen RJ. Org. Lett. 2004, 6: 2607

<A NAME="RZ17809SS-3">3</A> Williams DE. Keyzers RA. Warabi K. Desjardine K. Jenna L. Riffell JL. Roberge M. Andersen RJ. J. Org. Chem. 2007, 72: 9842

<A NAME="RZ17809SS-4">4</A> Warabi K. Williams DE. Patrick BO. Roberge M. Andersen RJ. J. Am. Chem. Soc. 2007, 129: 508

<A NAME="RZ17809SS-5A">5a</A> Liu J. Hsung RP. Org. Lett. 2005, 7: 2273

<A NAME="RZ17809SS-5B">5b</A> Paterson I. Anderson EA. Dalby SM. Loiseleur O. Org. Lett. 2005, 7: 4125

<A NAME="RZ17809SS-5C">5c</A> Paterson I. Anderson EA. Dalby SM. Loiseleur O. Org. Lett. 2005, 7: 4121

<A NAME="RZ17809SS-5D">5d</A> Liu J. Yang JH. Ko C. Hsung RP. Tetrahedron Lett. 2006, 47: 6121

<A NAME="RZ17809SS-5E">5e</A> Ghosh SK. Ko C. Liu J. Wang J. Hsung RP. Tetrahedron 2006, 62: 10485

<A NAME="RZ17809SS-5F">5f</A> Fürstner A. Fenster MDB. Fasching B. Godbout C. Radkowski K. Angew. Chem. Int. Ed. 2006, 45: 5510

<A NAME="RZ17809SS-5G">5g</A> Yang JH. Liu J. Hsung RP. Org. Lett. 2008, 10: 2525

<A NAME="RZ17809SS-5H">5h</A> Paterson I. Anderson EA. Dalby SM. Lim JH. Maltas P. Moessner C. Chem. Commun. 2006, 4186

<A NAME="RZ17809SS-5I">5i</A> Pan Y. De Brabander JK. Synlett 2006, 853

<A NAME="RZ17809SS-5J">5j</A> Wang C. Forsyth CJ. Org. Lett. 2006, 8: 2997

<A NAME="RZ17809SS-5K">5k</A> Paterson I. Anderson EA. Dalby SM. Genovino J. Lim JH. Moessner C. Chem. Commun. 2007, 1852

<A NAME="RZ17809SS-5L">5l</A> Fürstner A. Fenster MDB. Fasching B. Godbout C. Radkowski K. Angew. Chem. Int. Ed. 2006, 45: 5506

<A NAME="RZ17809SS-5M">5m</A> Fürstner A. Fasching B. O’Neil GW. Fenster MDB. Godbout C. Ceccon J. Chem. Commun. 2007, 3045

<A NAME="RZ17809SS-5N">5n</A> Wang C. Forsyth CJ. Heterocycles 2007, 72: 621

<A NAME="RZ17809SS-5O">5o</A> Smith AB. Kim D.-S. Org. Lett. 2007, 9: 3311

<A NAME="RZ17809SS-5P">5p</A> Keaton KA. Phillips AJ. Org. Lett. 2008, 10: 1083

<A NAME="RZ17809SS-5Q">5q</A> Chandrasekhar S. Rambabu C. Reddy AS. Org. Lett. 2008, 10: 4355

<A NAME="RZ17809SS-5R">5r</A> Paterson I. Anderson EA. Dalby SM. Lim JH. Genovino J. Maltas P. Moessner C. Angew. Chem. Int. Ed. 2008, 47: 3016

<A NAME="RZ17809SS-5S">5s</A> Paterson I. Anderson EA. Dalby SM. Lim JH. Genovino J. Maltas P. Moessner C. Angew. Chem. Int. Ed. 2008, 47: 3021

<A NAME="RZ17809SS-6A">6a</A> Newmann DJ. Cragg GM. J. Nat. Prod. 2007, 70: 461

<A NAME="RZ17809SS-6B">6b</A> Koehn FE. Carter GT. Nat. Rev. Drug Discovery 2005, 4: 206

<A NAME="RZ17809SS-6C">6c</A> Bialy L. Waldmann H. Angew. Chem. Int. Ed. 2005, 44: 3814

<A NAME="RZ17809SS-6D">6d</A> McCluskey A. Sim ATR. Sakoff JA. J. Med. Chem. 2002, 45: 1151

<A NAME="RZ17809SS-6E">6e</A> Honkanen RE. Golden T. Curr. Med. Chem. 2002, 9: 2055

<A NAME="RZ17809SS-7A">7a</A> Rychnovsky SD. Thomas CR. Org. Lett. 2000, 2: 1217

<A NAME="RZ17809SS-7B">7b</A> Yang X.-F. Mague JT. Li C.-J. J. Org. Chem. 2001, 66: 739

<A NAME="RZ17809SS-7C">7c</A> Barry CStJ. Crosby SR. Harding JR. Hughes RA. King CD. Parker GD. Willis CL. Org. Lett. 2003, 5: 2429

<A NAME="RZ17809SS-7D">7d</A> Crosby SR. Harding JR. King CD. Parker GD. Willis CL. Org. Lett. 2002, 4: 3407

<A NAME="RZ17809SS-7E">7e</A> Rychnovsky SD. Hu Y. Ellsworth B. Tetrahedron Lett. 1998, 39: 7271

<A NAME="RZ17809SS-7F">7f</A> Semeyn C. Blaauw RH. Hiemstra H. Speckamp WN. J. Org. Chem. 1997, 62: 3426

<A NAME="RZ17809SS-7G">7g</A> Cloninger MJ. Overman LE. J. Am. Chem. Soc. 1999, 121: 1092

<A NAME="RZ17809SS-7H">7h</A> Suginome M. Iwanami T. Ito Y. J. Org. Chem. 1998, 63: 6096

<A NAME="RZ17809SS-8">8</A> Sabitha G. Bhikshapathi M. Yadav JS. Tetrahedron Lett. 2006, 47: 2807

<A NAME="RZ17809SS-9A">9a</A> Sabitha G. Reddy KB. Reddy GSKK. Narjis F. Yadav JS. Synlett 2005, 2347

<A NAME="RZ17809SS-9B">9b</A> Sabitha G. Narjis F. Reddy EV. Yadav JS. Tetrahedron Lett. 2008, 49: 6087

<A NAME="RZ17809SS-9C">9c</A> Sabitha G. Narjis F. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry 2009, 20: 184

<A NAME="RZ17809SS-10">10</A> Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen E. J. Am. Chem. Soc. 2002, 124: 1307

<A NAME="RZ17809SS-11">11</A> Hansen TV. Tetrahedron: Asymmetry 2002, 13: 547

<A NAME="RZ17809SS-12">12</A> Sabitha G. Bhaskar V. Yadav JS. Tetrahedron Lett. 2006, 47: 8179

<A NAME="RZ17809SS-13">13</A> Holmquist CR. Roskamp EJ. J. Org. Chem. 1989, 54: 3258

<A NAME="RZ17809SS-14A">14a</A> Evans DA. Hoveyda AH. J. Am. Chem. 1990, 112: 6447

<A NAME="RZ17809SS-14B">14b</A> Schneider C. Klapa K. Hansch M. Synlett 2005, 91

<A NAME="RZ17809SS-14C">14c</A> La Cruz TE. Rychnovsky SD. J. Org. Chem. 2007, 72: 2602

<A NAME="RZ17809SS-15">15</A> Rychnovsky SD. Rogers B. Yang G. J. Org. Chem. 1993, 58: 3511