Fragment assembly: An alternative approach to generating complex polyketides

Synthetic Communications

Volumn 36, Issue 12, 2006, Pages 1735-1743

  Shaw, Simon J ^a   Zhang, Dan ^a   Sundermann, Kurt F ^a   Myles, David C ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

Chemobiosynthesis; Discodermolide; Polyketide

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; DICTYOSTATIN; DISCODERMOLIDE; KETONE; LACTONE; NATURAL PRODUCT; POLYKETIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MARINE ENVIRONMENT; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 33646795976     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600616784     Document Type: Article

References (16)

1. Myles, D. C. Novel biologically active natural and unnatural products. Curr. Opin. Biotechnol. 2003, 14, 627-633.
2. (a) Paterson, I.; Florence, G. J. The development of a practical total synthesis of discodermolide, a promising microtubule-stabilizing anticancer agent. Eur. J. Org. Chem. 2003, 12, 2193-2208;
3. For a review of discodermolide syntheses see; (b) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Serening, N. A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions. J. Am. Chem. Soc. 2001, 123, 9535-9544;
4. (c) Smith III, A. B.; Beauchamp, T. J.; LaMarche, M. J.; Kaufinan, M. D.; Qui, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. Evolution of a gram-scale synthesis of (+)-discodermolide. J. Am. Chem. Soc. 2000, 122, 8654-8664.
5. (a) Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Total synthesis and configurational assignment of (-)-dictyostatin, a microtubule-stabilizing macrolide of marine sponge origin. Angew. Chem. Int. Ed. 2004, 43, 4629-4633;
6. For recent dictyostatin syntheses see; (b) Shin, Y.; Fournier, J-H.; Fukui, Y.; Bruckner, A. M.; Curran, D. P. Total synthesis of (-)-dictyostatin: Confirmation of relative and absolute configurations. Angew. Chem. Int. Ed. 2004, 43, 4634-4637.
7. (a) Smith III, A. B.; Freeze, B. S.; Xian, M.; Hirose, T. Total synthesis of (+)-discodermolide: A highly convergent fourth generation approach. Org. Lett. 2005, 7, 1825-1828;
8. For recent advances in the discodermolide synthesis, see; (b) Paterson, I.; Delgado, O.; Florence, G. J.; Lyothier, I.; O'Brien, M.; Scott, J. P.; Sereinig, N. A second-generation total synthesis of (+)-discodermolide: The development of practical route using solely substrate-based stereocontrol. J. Org. Chem. 2005, 70, 150-160.
9. Mickel, S. J.; Sedelmeier, G. H.; Niederer, D.; Daeffler, R.; Osmani, A.; Schreiner, K.; Seeger-Weibel, M.; Berod, B.; Schaer, K.; Gamboni, R.; Chen, S.; Chen, W.; Jagoe, C. T.; Kinder, F. R., Jr.; Loo, M.; Prasad, K.; Repic, O.; Shieh, W.-C.; Wang, R.-M.; Waykole, L.; Xu, D. D.; Xue, S. Large-scale synthesis of the anticancer marine natural product (+)-discodermolide Org. Proc. Res. Dev. 2004, 8, 92-130.
10. (a) Burlingame, M. A.; Shaw, S. J.; Sundermann, K. F.; Zhang, D.; Petryka, J.; Mendoza, E.; Liu, F.; Myles, D. C.; LaMarche, M. J.; Hirose, T.; Freeze, B. S.; Smith III, A. B. Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues. Bioorg. Med. Chem. Lett. 2004, 14, 2335-2338;
11. (b) Shaw, S. J.; Sundermann, K. F.; Burlingame, M. A.; Myles, D. C.; Freeze, B. S.; Xian, M.; Brouard, I.; Smith III, A. B. Toward understanding how the lactone moiety of discodermolide affects activity. J. Am. Chem. Soc. 2005, 127, 6532-6533.
12. Kao, C. M.; Luo, G.; Katz, L.; Kane, D. E.; Khosla, C. Manipulation of macrolide ring size by directed mutagenesis of a modular polyketide synthase. J. Am. Chem. Soc. 1995, 117, 9105-9106.
13. Brown, M. J. B.; Cortes, J.; Cutter, L. A.; Leadley, P. F.; Stauton, J. A mutant generated by expression of an engineered DEBSI protein from the erythromycin-producing polyketide synthase (PKS) in Streptomyces coelicolor produces the triketide lactone, but the major product is the nor-analogue derived from acetate as starter acid. J. Chem. Soc., Chem. Commun. 1995, 1517-1578.
14. Corey, E. J.; Venkateswarlu, A. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J. Am. Chem. Soc. 1972, 94, 6190-6191.
15. Mickel, S. J.; Daeffler, R.; Prikoszovich, W. A study of the Paterson boron aldol reaction as used in the large-scale total synthesis of the anticancer marine natural product (+)-discodermolide. Org. Process Res. Dev. 2005, 9, 113-120.
16. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. Asymmetric aldol additions: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones and thiazolidinethiones. J. Org Chem 2001, 66, 894-902.