Synlett 2012; 23(10): 1446-1458
DOI: 10.1055/s-0031-1290967
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© Georg Thieme Verlag Stuttgart · New York

Method in the Madness – Methodology from Total Synthesis

Rebecca H. Pouwer
a   Eskitis Insitute for Cell and Molecular Therapies, Griffith University, Don Young Road, Nathan, QLD, 4111, Australia
,
Craig M. Williams*
b   School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, QLD, 4111, Australia, Fax: +61 7 33 65 42 99   eMail: c.williams3@uq.edu.au
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Publikationsverlauf

Received: 17. Dezember 2011

Accepted after revision: 11. Januar 2012

Publikationsdatum:
29. Mai 2012 (online)


Abstract

A review surveying the synthetic methodology developed by the Williams group over the last ten years, driven by natural product total synthesis, is presented. An underlying theme over this time has been the reliance on physical organic chemistry, organometallics and the cyclohexane ring system.

1 Introduction

2 Morita–Baylis–Hilman (MBH) Reaction

3 2-Iodoxybenzoic Acid (IBX)

4 Wittig Reagents

5 cis-Alkenes for 6π-Electrocyclisations

6 Ketal-Claisen Rearrangements

7 Silver(I) Acetylides

8 Photochemistry

9 Acyl Anion Equivalents

10 Conclusion

 
  • References

    • 1a Porzelle A, Williams CM, Schwartz BD, Gentle IR. Synlett 2005; 2923
    • 1b Schwartz BD, Porzelle A, Jack KS, Faber JM, Gentle IR, Williams CM. Adv. Synth. Catal. 2009; 351: 1148
  • 2 Porzelle A, Williams CM. Synthesis 2006; 3025
  • 3 Gallen MJ, Goumont R, Clark T, Terrier F, Williams CM. Angew. Chem. Int. Ed. 2006; 45: 2929
    • 4a Waters T, Boulton J, Clark T, Gallen MJ, Williams CM, O’Hair AJ. Org. Biomol. Chem. 2008; 6: 2530
    • 4b O’Hair RA. J, Williams CM, Clark T. J. Mol. Model. 2010; 16: 559
  • 5 Schwartz BD, Williams CM, Anders E, Bernhardt PV. Tetrahedron 2008; 64: 6482
    • 6a Schwartz BD, Denton JR, Davies HM. L, Williams CM. Aust. J. Chem. 2009; 62: 980

    • For our efforts towards the synthesis of vibsanin E, see:
    • 6b Schwartz BD, Williams CM, Bernhardt PV. Beilstein J. Org. Chem. 2008; 4: 34
    • 6c Schwartz BD, Denton JR, Lian Y, Davies HM. L, Williams CM. J. Am. Chem. Soc. 2009; 131: 8329
  • 7 Merritt AT, Pouwer RH, Williams DJ, Williams CM, Ley SV. Org. Biomol. Chem. 2011; 9: 4745
  • 8 Pouwer RH, Schill H, Williams CM, Bernhardt PV. Eur. J. Org. Chem. 2007; 4699
  • 9 Mirzayans PM, Pouwer RH, Williams CM. Org. Lett. 2008; 10: 3861
  • 10 Mirzayans PM, Pouwer RH, Williams CM, Bernhardt PV. Tetrahedron 2009; 65: 8297
  • 11 Stefani HA, Guadagnin RC, Keppler AF, Botteselle GV, Comasseto JV, Suganuma CA. Beilstein J. Org. Chem. 2008; 4: No 9
    • 12a Fang X, Zhang Q, Tan C.-J, Mu S.-Z, Lu Y, Lu Y.-B, Zheng Q.-T, Di Y.-T, Hao X.-J. Tetrahedron 2009; 65: 7408
    • 12b Baker LA, Williams CM, Bernhardt PV, Yanik GW. Tetrahedron 2006; 62: 7355
  • 13 Faber JM, Williams CM. Chem. Commun. 2011; 47: 2258
    • 14a Williams CM, Mander LN. Org. Lett. 2003; 5: 3499
    • 14b Williams CM, Mander LN, Bernhardt PV, Willis AC. Tetrahedron 2005; 61: 3759
    • 15a Pouwer RH, Williams CM. Silver Alkyls, Alkenyls, Aryls, and Alkynyls in Organic Synthesis, In Silver in Organic Chemistry . Harmata M. John Wiley & Sons, Inc; Hoboken / NJ / USA: 2010
    • 15b For other work regarding the reactions of silver acetylides, see: Proietti Silvestri I, Andemarian F, Khairallah GN, Wan YapS, Quach T, Tsegay S, Williams CM, O’Hair RA. J, Donnelly PS, Williams SJ. Org. Biomol. Chem. 2011; 9: 6082
  • 16 Pouwer RH, Williams CM, Raine AL, Harper JB. Org. Lett. 2005; 7: 1323
  • 17 Pouwer RH, Harper JB, Vyakaranam K, Michl J, Williams CM, Jessen CH, Bernhardt PV. Eur. J. Org. Chem. 2007; 241
  • 18 Chow S, Kress C, Albaek N, Jessen C, Williams CM. Org. Lett. 2011; 13: 5286
    • 19a Williams CM, Heim R, Brecknell DJ, Bernhardt PV. Org. Biomol. Chem. 2004; 2: 806
    • 19b Williams CM, Heim R, Bernhardt PV. Tetrahedron 2005; 61: 3771
  • 20 Linsenmeier AM, Williams CM, Braese S. J. Org. Chem. 2011; 76: 9127
  • 21 Dong L, Gordon VA, Grange RL, Johns J, Parsons PG, Porzelle A, Reddell P, Schill H, Williams CM. J. Am. Chem. Soc. 2008; 130: 15262
  • 22 Dong L, Schill H, Grange RL, Porzelle A, Johns JP, Parsons PG, Gordon VA, Reddell PW, Williams CM. Chem. Eur. J. 2009; 15: 11307
  • 24 Grange RL, Williams CM. Tetrahedron Lett. 2010; 51: 1158
  • 25 Eger WA, Grange RL, Schill H, Goumont R, Clark T, Williams CM. Eur. J. Org. Chem. 2011; 2548