Stereoselective synthesis of the atropisomers of myristinin B/C

Organic Letters

Volumn 8, Issue 9, 2006, Pages 1925-1927

  Maloney, David J ^a   Chen, Shengxi ^a   Hecht, Sidney M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVONOID; MYRISTININ B; MYRISTININ C;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DNA DAMAGE; STEREOISOMERISM; SYNTHESIS;

DNA DAMAGE; FLAVONOIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33646448124     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060511b     Document Type: Article

References (19)

1. (a) Hecht, S. M. J. Nat. Prod. 2000, 63, 158.
2. (b) Hecht, S. M. Pharm. Biol. 2003, 41, S68 and references therein.
3. Sawadjoon, S.; Kittakoop, P.; Kirtikara, K.; Vichai, V.; Tanticharoen, M.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 5470.
4. Compound 1 has also been isolated from Horsfieldia amygdaline. See: Katuhiko, H.; Akio, K.; Hirokazu, Y.; Akira, M.; Akira, I.; Akinori, S.; Shengji, P.; Yanhui, L.; Chun, W. Patent WO 9208712, 1992.
5. Deng, J.-Z.; Starck, S. R.; Li, S.; Hecht, S. M. J. Nat. Prod. 2005, 68, 1625.
6. Maloney, D. J.; Deng, J.-Z.; Starck, S. R.; Gao, Z.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 4140.
7. (a) Tückmantel, W.; Kozikowski, A. P.; Romanczyk, L. J., Jr. J. Am. Chem. Soc. 1999, 121, 12073.
8. (b) Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Tetrahedron 2002, 58, 7829.
9. (c) Kozikowski, A. P.; Tückmantel, W.; Hu, Y. J. Org. Chem. 2001, 66, 1287.
10. Notably, the enantiomer of 5 (i.e., having the 2S,3R configuration) can be obtained by using AD-Mix β in the asymmetric dihydroxylation7 reaction of 3.
11. Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585.
12. van Rensburg, H.; Steynberg, P. J.; Burger, J. F. W.; van Heerden, P. S.; Ferreira, D. J. Chem. Res., Synop. 1999, 450.
13. Initially, the use of MOM ethers was planned as they are generally more easily removed as compared to methyl ethers. However, all attempts to protect the three phenolic OH groups led to significant C-alkylation of the electron-rich aromatic ring.
14. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059.
15. 1H NMR spectra of the two compounds are quite different (see Supporting Information). The possibility that this species is a constitutional isomer of 1 formed under the forcing conditions cannot presently be excluded.
16. Attempts to measure the relative energies of compounds 1 and 2a,b using molecular modeling techniques led to inconsistent results.
17. 1H spectrum of 2a,b as these protons possess different resonances due to the restricted rotation about the substituents on C-4 and C-3′. Sawadajoon and co-workers2 reported the same ratio and assigned the structures of atropisomers 2a and 2b through NOESY spectral data by observing a cross-peak with the chelated hydroxyl (2′-OH) of 2a with the pseudoaxial H-4. In comparison, this correlation was absent in 2b.
18. See Supporting Information for the optical rotations of intermediates from the enantiomeric series.
19. 23D +44.6 (c 0.6, MeOH).