Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3674-3676

  Chin, Yen Jin ^a   Wang, Shun Yi ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIOLOGICAL PRODUCT; ESTER; IRIOMOTEOLIDE 1A; IRIOMOTEOLIDE-1A; MACROLIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; BIOLOGICAL PRODUCTS; CATALYSIS; ESTERS; MACROLIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 68949109676     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901480s     Document Type: Article

References (18)

1. The investigation of the Amphidinium strain HYA024 led to isolation of iriomoteolide-1a (1), -1b, and -1c. (a) Isolation and structural elucidation of iriomoteolide-1a (1): Tsuda, M.; Oguchi, K.; Iwamoto, R.; Okamoto, Y.; Kobayashi, J.; Fukushi, E.; Kawabata, J.; Ozawa, T.; Masuda, A.; Kitaya, Y.; Omasa, K. J. Org. Chem. 2007, 72, 4469.
2. (b) Isolation and structural elucidation of iriomoteolide-1b and -1c: Tsuda, M.; Oguchi, K.; Iwanmoto, R.; Okamoto, Y.; Fukushi, E.; Kawabata, J.; Ozawa, T.; Masuda, A. J. Nat. Prod. 2007, 70, 1661.
3. (a) Fang, L. J.; Xue, H. R.; Yang, J. Org. Lett. 2008, 10, 4645.
4. (b) Ghosh, A. K.; Yuan, H. Tetrahedron Lett. 2009, 50, 1416.
5. Xie, J.; Horne, D. A. Tetrahedron Lett. 2009, 50, 4485.
6. The diastereoselectivity and enantioselectivity were determined by comparison with the NMR spectroscopic and HPLC analytical results of diastereomers obtained from this paper: Nots, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
7. Nicolaou, K. C.; Li, H.-M.; Nold, A. L.; Pappo, D.; Lenzen, A. J. Am. Chem. Soc. 2007, 129, 10356.
8. Compound 11a has also been used in an alternative synthesis of the C13-C23 fragment (results submitted for publication).
9. Nishikawa, T.; Urabe, D.; Isobe, M. Angew. Chem., Int. Ed. 2004, 43, 4785.
10. Lum, T. K.; Wang, S. Y.; Loh, T. P. Org. Lett. 2008, 10, 761.
11. 13C NMR by comparing an average of carbon signals with respective diastereomeric mixtures of the acyclic carbon chain. The stereochemistry was assigned on the basis of enantiomeric Tol-BINAP ligands.
12. (a) Wang, S. Y.; Ji, S. J.; Loh, T. P. J. Am. Chem. Soc. 2007, 129, 276.
13. (b) Wang, S. Y.; Lum, T. K.; Ji, S. J.; Loh, T. P. Adv. Synth. Catal. 2008, 350, 673.
14. (a) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
15. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919.
16. Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M. J. Org. Chem. 1989, 54, 5930.
17. Paquette, L. A.; Chang, S. K. Org. Lett. 2005, 7, 3111.
18. Esteban, J.; Costa, A. M.; Vilarrasa, J. Org. Lett. 2008, 10, 4843.