Stereocontrolled total synthesis of apicularen A and its Δ17,18 Z isomer

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3701-3704

  Nicolaou, K C ^a,b   Kim, David W ^a,b   Baati, Rachid ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biomimetic synthesis; Macrolides; Natural products; Polyketides; Total synthesis

Indexed keywords

BIOSYNTHESIS; CARBON;

APICULAREN ANALOGUES; STEREOCONTROLLED TOTAL SYNTHESIS;

ISOMERS;

ACETIC ACID; ANTINEOPLASTIC AGENT; APICULAREN A; FUSED HETEROCYCLIC RINGS; NATURAL PRODUCT; POLYKETIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; ISOMER; ISOMERISM; MYXOCOCCALES; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; ISOMERISM; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 0037020381     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3701::AID-ANIE3701>3.0.CO;2-4     Document Type: Article

References (24)

1. B. Kunze, R. Jansen, F. Sasse, G. Höfle, H. Reichenbach, J. Antibiot. 1998, 51, 1075-1080.
2. R. Jansen, B. Kunze, H. Reichenbach, G. Höfle, Eur J. Org. Chem. 2000, 913-919.
3. a) A. Bhattacharjee, O. R. Seguil, J. K. De Brabander, Tetrahedron Lett. 2001, 42, 1217-1220;
4. b) for synthetic studies, see: A. Bhattacharjee, J. K. De Brabander, Tetrahedron Lett. 2000, 41, 8069-8073;
5. c) A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith, R. J. K. Taylor, Tetrahedron Lett. 2001. 42, 5549-5552:
6. d) M. Kuhnert, M. E. Maier, Org. Lett. 2002, 4, 643-646.
7. For the preparation of building block 3, see: a) A. Hadfield, H. Schweitzer, M. P. Trova, K. Green, Synth. Commun. 1991, 24, 1025-1029; b) A. Fürstner, I. Konetski, Tetrahedron 1996, 52, 15071-15078.
8. For the preparation of building block 3, see: a) A. Hadfield, H. Schweitzer, M. P. Trova, K. Green, Synth. Commun. 1991, 24, 1025-1029; b) A. Fürstner, I. Konetski, Tetrahedron 1996, 52, 15071-15078.
9. For the enantioselective allylboration of aldehydes, see: a) P. K. Jadhav, K. S. Bhat, P. T. Perumal, H. C. Brown, J. Org. Chem. 1986, 51, 432-439: b) U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401-404.
10. For the enantioselective allylboration of aldehydes, see: a) P. K. Jadhav, K. S. Bhat, P. T. Perumal, H. C. Brown, J. Org. Chem. 1986, 51, 432-439: b) U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401-404.
11. For the synthesis of the amide side chain 5 of apicularen, see: a) D. Labrecque, S. Charron, R. Rej, C. Blais, S. Lamothe, Tetrahedron Lett. 2001, 42, 2645-2648; b) A. Fürstner, T. Dierske, O. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298: c) B. B. Snider, F. Song, Org. Lett. 2002, 4, 407-408.
12. For the synthesis of the amide side chain 5 of apicularen, see: a) D. Labrecque, S. Charron, R. Rej, C. Blais, S. Lamothe, Tetrahedron Lett. 2001, 42, 2645-2648; b) A. Fürstner, T. Dierske, O. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298: c) B. B. Snider, F. Song, Org. Lett. 2002, 4, 407-408.
13. For the synthesis of the amide side chain 5 of apicularen, see: a) D. Labrecque, S. Charron, R. Rej, C. Blais, S. Lamothe, Tetrahedron Lett. 2001, 42, 2645-2648; b) A. Fürstner, T. Dierske, O. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298: c) B. B. Snider, F. Song, Org. Lett. 2002, 4, 407-408.
14. For the allylation of aromatic derivatives. see: a) A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 1557-1565; b) F.-T. Luo. R.-T Wang. Tetrahedron Lett. 1991, 32, 7703-7706; c) J. T. Feutrill, G. A. Holloway, F. Hilli, H. L. Huegel, M. A. Rizzacasa, Tetrahedron Lett. 2000, 41, 8569-8572.
15. For the allylation of aromatic derivatives. see: a) A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 1557-1565; b) F.-T. Luo. R.-T Wang. Tetrahedron Lett. 1991, 32, 7703-7706; c) J. T. Feutrill, G. A. Holloway, F. Hilli, H. L. Huegel, M. A. Rizzacasa, Tetrahedron Lett. 2000, 41, 8569-8572.
16. For the allylation of aromatic derivatives. see: a) A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 1557-1565; b) F.-T. Luo. R.-T Wang. Tetrahedron Lett. 1991, 32, 7703-7706; c) J. T. Feutrill, G. A. Holloway, F. Hilli, H. L. Huegel, M. A. Rizzacasa, Tetrahedron Lett. 2000, 41, 8569-8572.
17. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549.
18. H. Nakamura, K. Fujimaki, A. Murai, Tetrahedron Lett. 1996, 37, 3153-3156.
19. Previous eliminations of this type of bisamide with aldehydes led to mixtures of E and Z isomers of the corresponding acylenamine in relatively low yield, see ref. [6a].
20. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7409.
21. For the preparation of CuTC, see: G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749. For the synthesis of enamides with this reagent, see: R. Shen, J. A. Porco, Jr., Org. Lett. 2000, 9, 1333-1336.
22. For the preparation of CuTC, see: G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749. For the synthesis of enamides with this reagent, see: R. Shen, J. A. Porco, Jr., Org. Lett. 2000, 9, 1333-1336.
23. We thank Dr. R. Jansen of the Gesellschaft für Biotechnologische Forschung for kindly providing us with a sample of natural apicularen A.
24. We thank Prof. Paraskevi Giannakakou and Aurora O'Brate of the Winship Cancer Institute, Emory University School of Medicine, for these biological assays.