Total synthesis of (±)-phomactin B2 via an intramolecular cyclohexadienone annulation of a chromium carbene complex

Journal of the American Chemical Society

Volumn 129, Issue 44, 2007, Pages 13366-13367

  Huang, Jie ^a   Wu, Chunrui ^a   Wulff, William D ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CHROMIUM DERIVATIVE; CYCLOHEXADIENONE; CYCLOHEXANE DERIVATIVE; PHOMACTIN B2; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG; CHROMIUM; DRUG DERIVATIVE; EPOXIDE; FUSED HETEROCYCLIC RINGS; HYDROCARBON; METHANE; ORGANOMETALLIC COMPOUND;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIASTEREOISOMER; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CHROMIUM; CYCLIZATION; CYCLOHEXANES; EPOXY COMPOUNDS; HETEROCYCLIC COMPOUNDS, 3-RING; HYDROCARBONS; METHANE; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 35948969336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074275r     Document Type: Article

References (15)

1. For a review of the phomactins, see: Goldring, W. P. D.; Pattenden, G. Acc. Chem. Res. 2006, 39, 354-361.
2. (a) Tokiwano, T.; Fukushi, E.; Endo, T.; Oikawa, H. Chem. Commun. 2004, 1324-1325.
3. (b) Tokiwano, T.; Endo, T.; Tsukagoshi, T.; Goto, H.; Fukushi, E.; Oikawa, H. Org. Biomol. Chem. 2005, 2713-2722.
4. (c) Chow, S. Y.; Williams, H. J.; Pennington, J. D.; Nanda, S.; Reibenspies, J. H.; Scott, A. I. Tetrahedron 2007, 63, 6204-6209.
5. For leading citations, see: Huang, J.; Wang, H.; Wu, C.; Wulff, W. D. Org. Lett. 2007, 9, 2799-2802.
6. For the total syntheses of phomactins, see: phomactin D: (a) Miyaoka, H.; Saka, Y.; Miura, S.; Yamada, Y. Tetrahedron Lett. 1996, 37, 7107-7110.
7. Phomactin A: (b) Goldring, W. P. D.; Pattenden, G. Chem. Commun. 2002, 1736-1737.
8. (c) Mohr, P. J.; Halcomb, R. L. J. Am. Chem. Soc. 2003, 125, 1712-1713.
9. (d) Diaper, C. M.; Goldring, W. P. D.; Pattenden, G. Org. Biomol. Chem. 2003, 3949-3956.
10. Phomactin G: (e) Goldring, W. P. D.; Pattenden, G. Org. Biomol. Chem. 2004, 466-473.
11. Hsung, R. P.; Quinn, J. F.; Weisenberg, B. A.; Wulff, W. D.; Yap, G. P. A.; Rheingold, A. L. Chem. Commun. 1997, 615-616.
12. Armstrong, R.; Weiler, L. Can. J. Chem. 1983, 61, 2530-2539.
13. Negishi, E.; Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639-6647.
14. Aumann, R.; Fischer, E. O. Chem. Ber. 1968, 101, 954-962.
15. Hirao, T. Chem. Rev. 1997, 97, 2707-2724.