Total synthesis of (-)-incarvilline

Tetrahedron Letters

Volumn 46, Issue 13, 2005, Pages 2327-2329

  Ichikawa, Masaya ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

( ) Incarvilline; Cyclobutane ring opening; Intramolecular 2+2 photocycloaddition; Three component coupling

Indexed keywords

ALKENE; CYCLOBUTANE; INCARVILLINE; IODINE DERIVATIVE; NATURAL PRODUCT; SAMARIUM; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLOADDITION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; RING OPENING;

EID: 14744286773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.173     Document Type: Article

References (13)

1. Y.-M. Chi, W.-M. Yan, D.-C. Chen, H. Noguchi, Y. Iitaka, and U. Sankawa Phytochemistry 31 1992 2930 2932
2. Y.-M. Chi, W.-M. Yan, and J.-S. Li Phytochemistry 29 1990 2376 2378
3. M. Nakamura, Y.-M. Chi, W.-M. Yan, Y. Nakasugi, T. Yoshizawa, N. Irino, F. Hashimoto, J. Kinjo, T. Nohara, and S. Sakurada J. Nat. Prod. 62 1999 1293 1294
4. Y.-M. Chi, F. Hashimoto, W.-M. Yan, T. Nohara, M. Yamashita, and N. Marubayashi Chem. Pharm. Bull. 45 1997 495 498
5. M. Ichikawa, M. Takahashi, S. Aoyagi, and C. Kibayashi J. Am. Chem. Soc. 126 2004 16553 16558
6. For an extensive review of synthetic application of intramolecular enone-olefin photocycloadditions, see: M.T. Crimmins Chem. Rev. 88 1988 1453 1473
7. For a review on 'three-component coupling', see: R. Noyori, and M. Suzuki Angew. Chem., Int. Ed. Engl. 23 1984 847 876
8. For a review of reduction with samarium(II) iodide, see: G.A. Molander Org. React. 46 1994 211 367
9. 2, see: D.L. Commins, and X. Zheng J. Chem. Soc., Chem. Commun. 1994 2681 2682
10. D.L. Commins, Y.-M. Zhang, and X. Zheng Chem. Commun. 1998 2509 2510
11. D.L. Commins, X. Zheng, and R.R. Goehring Org. Lett. 4 2002 1611 1613
12. W.D. Shipe, and E.J. Sorensen Org. Lett. 4 2002 2063 2066
13. For a review, see: T. Shintou, W. Kikuchi, and T. Mukaiyama Bull. Chem. Soc. Jpn. 76 2003 1645 1667