Total synthesis of the fumiquinazoline alkaloids: Solid-phase studies

Journal of Combinatorial Chemistry

Volumn 2, Issue 2, 2000, Pages 186-194

  Wang, Haishan ^a   Ganesan, A ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTHRANILIC ACID DERIVATIVE; OLIGOPEPTIDE; PEPTIDE LIBRARY; QUINAZOLINE DERIVATIVE;

ARTICLE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALKALOIDS; ANTHRANILIC ACIDS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; PEPTIDE LIBRARY; QUINAZOLINES;

EID: 0034153217     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9900807     Document Type: Article

References (16)

1. (1) Abbreviations: Ala = Alanine, EDC = 1-ethyl-3-(3-(diethylamino)-propyl)carbodiimide·HCl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl, Gly = glycine, Leu = leucine, Phe = phenylalanine, Trp = tryptophan.
2. Demethoxyfumitremorgin C and luotonin A: (a) Wang, H.; Ganesan, A. Concise Synthesis of the Cell Cycle Inhibitor Demethoxyfumitremorgin C. Tetrahedron Lett. 1997, 38, 4327-4328.
3. (b) Wang, H.; Ganesan, A. The N-Acyliminium Pictet-Spengler Condensation as a Multicomponent Combinatorial Reaction on Solid Phase and its Application to the Synthesis of Demethoxyfumitremorgin C Analogues. Org. Lett. 1999, 1, 1647-1649.
4. (c) Wang, H.; Ganesan, A. Total Synthesis of the Cytotoxic Alkaloid Luotonin A. Tetrahedron Lett. 1998, 39, 9097-9098.
5. (a) Communication: Wang, H.; Ganesan, A. Total Synthesis of the Quinazoline Alkaloids (-)-Fumiquinazoline G and (-)-Fiscalin B. J. Org. Chem. 1998, 63, 2432-2433.
6. (b) Full paper: Wang, H.; Ganesan, A. Total Synthesis of the Fumiquinazoline Alkaloids: Solution-phase Studies. J. Org. Chem. 2000, 65, 1022-1030.
7. For recent reviews, see: (a) Bunin, B. A. The Combinatorial Index; Academic: San Diego, 1998.
8. (b) Brown, R. C. D. Recent Developments in Solid-Phase Organic Synthesis. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320.
9. (c) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Solid-phase Organic Reactions III: A Review of the Literature Nov 96-Dec 97. Tetrahedron 1998, 54, 15385-15443.
10. (a) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. An Expedient and High-Yielding Method for the Solid-Phase Synthesis of Diverse 1,4-Benzodiazepine-2,5-Diones. J. Org. Chem. 1995, 60, 5742-5743.
11. (b) Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. A. Solid-phase Synthesis Of 1,4-Benzodiazepine-2,5-Diones. Library Preparation and Demonstration of Synthesis Generality. J. Org. Chem. 1997, 62, 1240-1256.
12. Carpino, L. A.; Chao, H. G.; Beyermann, M.; Bienert, M. ((9-Fluorenylmethyl)oxy)Carbonyl Amino-Acid Chlorides in Solid-Phase Peptide-Synthesis. J. Org. Chem. 1991, 56, 2635-2642.
13. (a) Ellman, J. A.; Bunin, B. A. A General and Expedient Method for the Solid-Phase Synthesis of 1,4-Benzodiazepine Derivatives. J. Am. Chem. Soc. 1992, 114, 10997-10998.
14. (b) Ellman, J. A.; Plunkett, M. J. Germanium and Silicon Linking Strategies for Traceless Solid-Phase Synthesis. J. Org. Chem. 1997, 62, 2885-2893.
15. Product release by a cyclization reaction was first described by Rapoport: (a) Crowley, J. I.; Rapoport, H. Cyclization via Solid-Phase Synthesis. Unidirectional Dieckmann Products from Solid Phase and Benzyl Triethylcarbinyl Pimelates. J. Am. Chem. Soc. 1970, 92, 6363-6365.
16. (b) Crowley J. I.; Rapoport H. Unidirectional Dieckmann Cyclizations on a Solid Phase and in Solution. J. Org. Chem. 1980, 45, 3215-3227.