Total Synthesis of (+)-Macquarimicin A

Journal of the American Chemical Society

Volumn 125, Issue 48, 2003, Pages 14722-14723

  Munakata, Ryosuke ^a   Katakai, Hironori ^a   Ueki, Tatsuo ^a   Kurosaka, Jun ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC ANTIBIOTIC; COCHLEAMYCIN A; FR 182877; MACQUARIMICIN A; STABILIZING AGENT; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; GEOMETRY; MICROTUBULE; REDUCTION; STEREOCHEMISTRY;

MACROLIDES; MICROMONOSPORA; STEREOISOMERISM;

EID: 0344861891     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038732p     Document Type: Article

References (28)

1. (a) Jackson, M.; Karwowski, J. P.; Theriault, R. J.; Rasmussen, R. R.; Hensey, D. M.; Humphrey, P. E.; Swanson, S. J.; Barlow, G. J.; Premachandran, U.; McAlpine, J. B. J. Antibiot. 1995, 48, 462.
2. (b) Hochlowski, J. E.; Mullally, M. M.; Henry, R.; Whittem, D. M.; McAlpine, J. B. J. Antibiot. 1995, 48, 467.
3. Tanaka, M.; Nara, F.; Yamasato, Y.; Masuda-Inoue, S.; Doi-Yoshioka, H.; Kumakura, S.; Enokita, R.; Ogita, T. J. Antibiot. 1999, 52, 670.
4. Shindo, K.; Matsuoka, M.; Kawai, H. J. Antibiot. 1996, 49, 241.
5. (a) Sato, B.; Muramatsu, H.; Miyauchi, M.; Hori, Y.; Takase, S.; Hino, M.; Hashimoto, S.; Terane, H. J. Antibiot. 2000, 53, 123.
6. (b) Yoshimura, S.; Sato, B.; Kinoshita, T.; Takase, S.; Terano, H. J. Antibiot. 2002, 55, C-1.
7. (a) Shindo, K.; Sakakibara, M.; Kawai, H.; Seto, H. J. Antibiot. 1996, 49, 249.
8. (b) Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393.
9. (c) Recent review on the topic: Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078.
10. Synthetic studies: (a) Cochleamycin A: Chang, J.; Paquette, L. A. Org. Lett. 2002, 4, 253.
11. (b) FR182877: ref 5b and references therein.
12. Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. See also ref 5b for total synthesis of (-)-3.
13. Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. 2002, 41, 1787.
14. Tatsuta, K.; Narazaki, F.; Kashiki N.; Yamamoto, J.; Nakano, S. J. Antibiot. 2003, 56, 584.
15. Macquarimicin A was originally reported to have E geometry concerning the C(2)-C(3) double bond. However, we assumed the correct structure of macquarimicin A to be I on the basis of the spectroscopic similarity to 2.
16. Preliminary study on our IMDA approach: Munakata, R.; Ueki, T.; Katakai, H.; Takao, K.; Tadano, K. Org. Lett. 2001, 3, 3029.
17. Recent review on TADA: Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243.
18. Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
19. Takano, S.; Kamikubo, T.; Sugihara, T.; Suzuki, M.; Ogasawara, K. Tetrahedron: Asymmetry 1993, 4, 201.
20. Grunwell, J. R.; Karapides, A.; Wigal, C. T.; Heinzman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91.
21. Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
22. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. I 1996, 2417.
23. Han, X.; Stoltz, B. M.; Corey, E. J. Am. Chem J. Soc. 1999, 121, 7600.
24. Extensive investigation on the coupling reaction revealed that the use of CuCl and the protection of the primary alcohol are essential to suppress the intramolecular Heck-type reaction of the (Z)-alkenylstannane.
25. Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177.
26. Review: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
27. 1H NMR spectrum, making elucidation of the E/Z ratio difficult. We attribute the complication to the tautomerization of 5 (such as ketalization), in addition to the geometry of the C(2)-C(3) double bond.
28. A TADA substrate without the lactone ring did not afford the desired cycloadduct.