Studies directed toward the total synthesis of lancifodilactone G: An expeditious route to the ABC subunit

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2111-2113

  Paquette, Leo A ^a   Kwong, Wah Lai ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL RADICAL; LANCIFODILACTONE G; TRITERPENE;

ARTICLE; CHEMISTRY; MEDICINAL PLANT; SCHISANDRACEAE; SYNTHESIS;

HYDROXYL RADICAL; PLANTS, MEDICINAL; SCHISANDRA; TRITERPENES;

EID: 51549107852     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800418m     Document Type: Article

References (20)

1. For the isolation and biological evaluation of lancifodilactone G, see: (a) Xiao, W.-L.; Zhu, H.-J.; Shen, Y.-H.; Li, R.-T.; Li, S.-H.; Sun, H.-D.; Zheng, Y.-T.; Wang, R.-R.; Lu, Y.; Wang, C.; Zheng, Q. T. Org. Lett. 2005, 7, 2145.
2. The original structural assignment for lancifodilactone G has been revised, see: (a) Xiao, W.-L.; Zhu, H.-J.; Shen, Y.-H.; Li, R.-T.; Li, S.-H.; Sun, H.-D.; Zheng, Y.-T.; Wang, R.-R.; Lu, Y.; Wang, C.; Zheng, Q. T. Org. Lett. 2006, 8, 801.
3. For the absolute configuration of micrandilactone B, see: (a) Huang, S.-X.; Li, R.-T.; Liu, J.-P.; Lu, Y.; Chang, Y.; Lei, C.; Xiao, W.-L.; Yang, L.-B.; Zheng, Q.-T.; Sun, H.-D Org. Lett. 2007, 9, 2079.
4. (b) For preliminary synthetic studies aimed at micrandilactone A, consult: Zhang, Y.-D.; Ren, W.-W.; Lan, Y.; Xiao, Q.; Wang, K.; Xu, J.; Chen, J.-H.; Yang, Z. Org. Lett. 2008, 10, 665.
5. The carbon numbering is assigned according to the system of the parent natural product in ref 1.
6. For reviews on the biomimetic synthesis of natural products, see: (a) Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730.
7. (b) Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757.
8. For reviews on cross-metathesis, see: (a) Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3171.
9. (c) Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417.
10. (d) Chatter, A. K.; Grubbs, R. H. Angew. Chem. Int. Ed. 2002, 41, 3171, and references cited therein.
11. Reviews on enyne metathesis, see: (a) Chattopadhyay, S. K.; Karmakar, S.; Biswas, T.; Majumdar, K. C.; Hahaman, H.; Roy, B. Tetrahedron 2007, 63, 3919.
12. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D Angew. Chem., Int. Ed. 2005, 44, 4490.
13. (c) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
14. Fontana, A. F.; Messina, R.; Spinella, A.; Cimino, G Tetrahedron Lett. 2000, 41, 7559. The diastereopurity of 2 was further ascertained by Mosher ester analysis (dr ≥ 20:1)
15. (a) Juaristi, E.; Jimenez-Vazquez, H. A. J. Org. Chem. 1991, 56, 1623.
16. (b) Samsel, E. G.; Kochi, J. K. Inorg. Chem. 1986, 25, 2450.
17. For IBX oxidation, see: (a) Frigerio, N.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
18. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 107.
19. 4 led to a low reaction rate and poor chemical yield. For chiral dihydroxylation catalysts in enantioselective synthesis, see: (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B Chem. Rev. 1994, 94, 2483. The stereochemistry of 15 was determined by spectral comparison with the advanced compound 21.
20. Diagnostic NOE enhancements between H-1 and H-19 and H-1 and H-30 were observed.