Assignment of the absolute configuration of the marine pentacyclic polyether (+)-enshuol by total synthesis

Angewandte Chemie - International Edition

Volumn 46, Issue 34, 2007, Pages 6481-6484

  Morimoto, Yoshiki ^a   Yata, Hiromi ^a   Nishikawa, Yoshihiro ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Asymmetric synthesis; Configuration determination; Structure elucidation; Terpenoids; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; BIOGENETIC CONSIDERATIONS; CONFIGURATION DETERMINATION; STRUCTURE ELUCIDATION; TERPENOIDS; TOTAL SYNTHESIS;

CYCLIC VOLTAMMETRY; GENETIC ENGINEERING; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

POLYETHERS;

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENSHUOL; EPOXIDE; ETHER DERIVATIVE; MARINE TOXIN; TRITERPENE;

ARTICLE; CHEMISTRY; CONFORMATION; RED ALGA; STEREOISOMERISM;

EPOXY COMPOUNDS; ETHERS, CYCLIC; INDICATORS AND REAGENTS; MARINE TOXINS; MOLECULAR CONFORMATION; RHODOPHYTA; STEREOISOMERISM; TRITERPENES;

EID: 34548299145     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701737     Document Type: Article

References (25)

1. For a review, see: J. J. Fernández, M. L. Souto, M. Norte, Nat. Prod. Rep. 2000, 17, 235-246.
2. Y. Matsuo, M. Suzuki, M. Masuda, Chem. Lett. 1995, 1043-1044.
3. K. C. Nicolaou, S. A. Snyder, Angew. Chem. 2005, 117, 1036-1069;
4. Angew. Chem. Int. Ed. 2005, 44, 1012-1044.
5. For the stereochemical assignment of oxasqualenoid structures by total synthesis, see: a) H. Kigoshi, M. Ojika, Y. Shizuri, H. Niwa, K. Yamada, Tetrahedron 1986, 42, 3789-3792;
6. b) Y. Morimoto, T. Iwai, T. Kinoshita, J. Am. Chem. Soc. 2000, 122, 7124-7125;
7. c) Z. Xiong, E. J. Corey, J. Am. Chem. Soc. 2000, 122, 9328-9329;
8. d) Y. Morimoto, T. Iwai, T. Kinoshita, Tetrahedron Lett. 2001, 42, 6307-6309;
9. e) H. Kigoshi, T. Itoh, T. Ogawa, K. Ochi, M. Okada, K. Suenaga, K. Yamada, Tetrahedron Lett. 2001, 42, 7461-7464;
10. f) Y. Morimoto, M. Takaishi, T. Iwai, T. Kinoshita, H. Jacobs, Tetrahedron Lett. 2002, 43, 5849-5852;
11. g) Y. Morimoto, Y. Nishikawa, M. Takaishi, J. Am. Chem. Soc. 2005, 127, 5806-5807;
12. h) Y. Morimoto, T. Okita, M. Takaishi, T. Tanaka, Angew. Chem. 2007, 119, 1150-1153;
13. Angew. Chem. Int. Ed. 2007, 46, 1132-1135.
14. Y. Morimoto, M. Takaishi, N. Adachi, T. Okita, H. Yata, Org. Biomol. Chem. 2006, 4, 3220-3222.
15. M. Suzuki, Y. Matsuo, S. Takeda, T. Suzuki, Phytochemistry 1993, 33, 651-656.
16. a) Y. Morimoto, Y. Nishikawa, C. Ueba, T. Tanaka, Angew. Chem. 2006, 118, 824-826;
17. Angew. Chem. Int. Ed. 2006, 45, 810-812;
18. b) Z. Xiong, E. J. Corey, J. Am. Chem. Soc. 2000, 122, 4831-4832.
19. 13C NMR, and IR spectroscopy, and by low- and high-resolution mass spectrometry (see the Supporting Information).
20. E. J. Corey, M. C. Noe, W.-C. Shieh, Tetrahedron Lett. 1993, 34, 5995-5998.
21. Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11 224-11 235.
22. A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939-1942.
23. a) J.-P. Bégué, D. Bonnet-Delpon, B. Crousse, Synlett 2004, 18-29;
24. b) A. Zakarian, A. Batch, R. A. Holton, J. Am. Chem. Soc. 2003, 125, 7822-7824 .
25. 2CHOH; however, the highest yield of 22 in these experiments was 10%.