Towards the Total Synthesis
of 3-Hydroxyvibsanin E

Brett D. Schwartz; Justin R. Denton; Paul V. Bernhardt; Huw M. L. Davies; Craig M. Williams

doi:10.1055/s-0029-1216912

PAPER

Towards the Total Synthesis of 3-Hydroxyvibsanin E

Brett D. Schwartz^a, Justin R. Denton^b, Paul V. Bernhardt^a, Huw M. L. Davies*^c, Craig M. Williams*^a
^a School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Queensland, Australia
Fax: +61(7)33654299; e-Mail: c.williams3@uq.edu.au;
^b Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA
^c Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA
Fax: +1(404)7277766; e-Mail: hmdavie@emory.edu;

Abstract

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Abstract

The synthesis of a silyl-protected derivative of 3-hydroxyvibsanin E has been achieved. The key step is a regio- and stereoselective C-H hydroxylation of an advanced tricyclic intermediate by means of a Rubottom oxidation.

Key words

hydroxyvibsanin E - C-H hydroxylation - Rubottom oxidation

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References

<A NAME="RC02509SS-1">1</A> Fukuyama Y. Minami H. Kagawa M. Kodama M. Kawazu K. J. Nat. Prod. 1999, 62: 337

<A NAME="RC02509SS-2">2</A> Fukuyama Y. Minami H. Fujii H. Tajima M. Phytochemistry 2002, 60: 765

<A NAME="RC02509SS-3">3</A> Fukuyama Y. Esumi T. J. Synth. Org. Chem., Jpn. 2007, 65: 585

<A NAME="RC02509SS-4">4</A> Wang L.-Q. Chen Y.-G. Xu J.-J. Liu Y. Li X.-M. Zhao Y. Chem. Biodiversity 2008, 5: 1879

<A NAME="RC02509SS-5">5</A> Fukuyama Y. Morisaki M. Minoshima Y. Minami H. Takahashi H. Asakawa Y. Lett. Org. Chem. 2004, 1: 189

<A NAME="RC02509SS-6">6</A> Fukuyama Y. Kubo M. Fujii T. Matsuo A. Minoshima Y. Minami H. Morisaki M. Tetrahedron 2002, 58: 10033

<A NAME="RC02509SS-7">7</A> Cryle MJ. Stok JE. De Voss JJ. Aust. J. Chem. 2003, 56: 749

<A NAME="RC02509SS-8">8</A> Schwartz BD. Denton JR. Lian Y. Davies HML. Williams CM. J. Am. Chem. Soc. 2009, 131: 8329

<A NAME="RC02509SS-9">9</A> Schwartz BD. Denton JR. Davies HML. Williams CM. Aust J. Chem. DOI: 10.1071/CH09267

<A NAME="RC02509SS-10A">10a</A> Davies HML. Loe Ø. Stafford DG. Org. Lett. 2005, 7: 5561

<A NAME="RC02509SS-10B">10b</A> Nikolai J. Loe Ø. Dominiak PM. Gerlitz OO. Autschbach J. Davies HML. J. Am. Chem. Soc. 2007, 129: 10763

<A NAME="RC02509SS-11A">11a</A> Gallen MJ. Williams CM. Org. Lett. 2008, 10: 713

<A NAME="RC02509SS-11B">11b</A> Gallen MJ. Goumont R. Clark T. Terrier F. Williams CM. Angew. Chem. Int. Ed. 2006, 45: 2929

<A NAME="RC02509SS-11C">11c</A> Gallen MJ. Williams CM. Eur. J. Org. Chem. 2008, 4697

<A NAME="RC02509SS-11D">11d</A> Tilly DP. Williams CM. Bernhardt PV. Org. Lett. 2005, 7: 5155

<A NAME="RC02509SS-11E">11e</A> Heim R. Wiedemann S. Williams CM. Bernhardt PV. Org. Lett. 2005, 7: 1327

<A NAME="RC02509SS-11F">11f</A> Schwartz BD. Tilly DP. Heim R. Wiedemann S. Williams CM. Bernhardt PV. Eur. J. Org. Chem. 2006, 3181

<A NAME="RC02509SS-11G">11g</A> Schwartz BD. Williams CM. Bernhardt PV. Beilstein J. Org. Chem. 2008, 4: 34

<A NAME="RC02509SS-11H">11h</A> Schwartz BD. Williams CM. Anders E. Bernhardt PV. Tetrahedron 2008, 64: 6482

<A NAME="RC02509SS-11I">11i</A> Chen AP.-J. Williams CM. Org. Lett. 2008, 10: 3441

For recent examples of selective C-H hydroxylation applied to natural product synthesis, see:

<A NAME="RC02509SS-12A">12a</A> Chen K. Baran PS. Nature 2009, in press

<A NAME="RC02509SS-12B">12b</A> Kim J. Ashenhurst JA. Movassaghi M. Science 2009, 324: 238

<A NAME="RC02509SS-12C">12c</A> Chen MS. White MC. Science 2007, 318: 783

<A NAME="RC02509SS-12D">12d</A> Wender PA. Hilinski MK. Mayweg AVW. Org. Lett. 2005, 7: 79

<A NAME="RC02509SS-13">13</A> Koser GF. Relenyi AG. Kalos AN. Rebrovic L. Wettach RH. J. Org. Chem. 1982, 47: 2487

<A NAME="RC02509SS-14">14</A> Davis FA. Chattopadhyay S. Towson JC. Lal S. Reddy T. J. Org. Chem. 1988, 53: 2087

<A NAME="RC02509SS-15">15</A> Rubottom GM. Vasquez MA. Pelegrina DR. Tetrahedron Lett. 1974, 4319

<A NAME="RC02509SS-16A">16a</A> Anders E. Gassner T. Angew. Chem., Int. Ed. Engl. 1982, 21: 289

<A NAME="RC02509SS-16B">16b</A> Anders E. Gaßner T. Angew. Chem. Suppl. 1982, 675

<A NAME="RC02509SS-16C">16c</A> Anders E. Gassner T. Angew. Chem., Int. Ed. Engl. 1983, 22: 619

<A NAME="RC02509SS-16D">16d</A> Anders E. Gaßner T. Chem. Ber. 1984, 117: 1034

<A NAME="RC02509SS-16E">16e</A> Anders E. Gaßner T. Stankowiak A. Chem. Ber. 1985, 118: 124

<A NAME="RC02509SS-16F">16f</A> Anders E. Clark T. Gaßner T. Chem. Ber. 1986, 119: 1350

<A NAME="RC02509SS-17A">17a</A> Linderman RJ. Godfrey A. Horne K. Tetrahedron 1989, 45: 495

<A NAME="RC02509SS-17B">17b</A> Mander LN. Thomson RJ. J. Org. Chem. 2005, 70: 1654

<A NAME="RC02509SS-18A">18a</A> Kadota I. Yamamoto Y. J. Org. Chem. 1998, 63: 6597

<A NAME="RC02509SS-18B">18b</A> Nicolaou KC. Reddy KR. Skokotas G. Sato F. Xiao X.-Y. J. Am. Chem. Soc. 1992, 114: 7935

<A NAME="RC02509SS-19">19</A> Perin DD. Armarego WLF. Purification of Laboratory Chemicals 3rd ed.: Pergamon; New York: 1988.

Crystallographic data for structures 24, 26, and 27 have been deposited with the Cambridge Crystallographic Data Centre (CCDC 737635-737637) and may be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, or e-mail: deposit@ccdc.cam.ac.uk.