Synthetic studies toward pectenotoxin 2. Part II. Synthesis of the CDE and CDEF ring systems

Organic Letters

Volumn 10, Issue 19, 2008, Pages 4183-4185

  Helmboldt, Hannes ^a   Aho, Jatta E ^a   Pinko, Petri M ^b  

^a AALTO UNIVERSITY   (Finland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; KETONE; PECTENOTOXIN 2; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

FURANS; KETONES; PYRANS;

EID: 55449096098     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801585j     Document Type: Article

References (23)

1. Aho, J. E.; Salomäki, E.; Rissanen, K.; Pihko, P. M. Org. Lett. 2008, 10, 4179-4182.
2. (a) Fischer, R.; Hoffmann, W.; Langguth, E.; Siegel, H. Eur. Pat. Appl. 1995 4179-4182.
3. (b) Silvestri, M. A.; He, C.; Khoram, A.; Lepore, S. D. Tetrahedron Lett. 2006, 47, 1625-1626.
4. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961.
5. Kawashima, M.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1988, 61, 4051-4055. Other methods of (E)-olefin construction, such as Julia-Kocienski olefination, gave remarkably inferior E:Z selectivities.
6. (a) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785-3786.
7. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
8. 2O is used. The commercially available AD-mix β contains about 0.4 mol % of catalyst. (2) The reaction was run only to ca. 30% conversion, and the remaining starting material was recycled. (3) Use of transesterification catalyst, 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD), to ensure complete lactone formation. See: Schuchardt, U.; Sercheli, R.; Vargas, R. M. J. Braz. Chem. Soc. 1998, 9, 199-210.
9. A benzoate derivative was used for ee determination (see Supporting Information).
10. (a) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.
11. (b) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933-2935.
12. (c) Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. J. Org. Chem. 1991, 56, 2299-2311.
13. For a recent review, see: (d) Härtung, J.; Greb, M. J. Organomet. Chem. 2002, 667, 67-84.
14. The use of CHP instead of TBHP and the presence of molecular sieves greatly improved the reproducibility of this reaction, but no change in the diastereoselectivity was observed.
15. Iversen, T.; Bundle, D. R. J. Chem. Soc., Chem. Commun. 1981, 1240-1241.
16. Griffith, W. P.; Ley, S. V.; Whitecombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627.
17. (a) Ukaji, Y.; Kanda, H.; Yamamoto, K.; Fujisawa, T. Chem. Lett. 1990, 597-600.
18. (b) Ruano, J. L. G.; Tito, A.; Culebras, R. Tetrahedron 1996, 52, 2177-2186.
19. 3 gave finally in all cases reproducible results.
20. Presumably, the presence of additional chelating groups (benzyl ether, two THF ring units) in 17 interferes with the reaction.
21. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807-810.
22. For a review of nonanomeric spiroketals, see: Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406-4440.
23. ∼50% of the isomerization of 20 to 21 occurred within 5 min (see Supporting Information for details). For the synthesis and characterization of 20 and 21, see: Pihko, P. M.; Aho, J. E. Org. Lett. 2004, 6, 3849-3852.