Synthesis of Porritoxin

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 2191-2193

  Cornella, Ivan ^a   Kelly, T Ross ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; IRON; MOLECULAR STRUCTURE;

KEY REACTIONS;

SYNTHESIS (CHEMICAL);

HEMPA; NATURAL PRODUCT; PORRITOXIN; TOXIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CYCLIZATION; DRUG ISOLATION; GRIGNARD REACTION; LITHIATION; MELTING POINT; PRENYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

BIOLOGICAL FACTORS; DIMETHYLFORMAMIDE; FORMIC ACID ESTERS; FORMIC ACIDS; INDOLES; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 1642296712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0356210     Document Type: Article

References (15)

1. Suemitsu, R.; Ohnishi, K.; Horiuchi, M.; Kitaguchi, A.; Odamura, K. Phytochemistry 1992, 31, 2325-2326.
2. Horiuchi, M.; Maoka, T.; Iwase, N.; Ohnishi, K. J. Nat. Prod. 2002, 65, 1204-1205.
3. Ayer, W. A.; Miao, S. Can. J. Chem. 1993, 71, 487-493.
4. Chen, C.-W.; Beak, P. J. Org. Chem. 1986, 51, 3325-3334.
5. The conversion of 12 to 14 had already been reproduced in good yield in our laboratories (Scopton, A.; Kelly, T. R., unpublished results).
6. (a) Hauser, F. M.; Hewawasam, P.; Baghdanov, V. M. J. Org. Chem. 1988, 53, 223-224.
7. (b) Evans, J. C.; Klix, R. C.; Bach, R. D. J. Org. Chem. 1988, 53, 5519-5527.
8. (c) Parker, K. A.; Spero, D. M.; Koziski, K. A. J. Org. Chem. 1987, 52, 183-188.
9. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 1381-1383.
10. Yamashita, M.; Miyoshi, K.; Nakazono, Y.; Suemitsu, R. Bull. Chem. Soc. Jpn. 1982, 55, 1663-1664.
11. Kelly, T. R.; Dali, H. M.; Tsang, W.-G. Tetrahedron Lett. 1977, 3859-3860.
12. 3SNa, see: Kornblum, N.; Scott, A. J. Am. Chem. Soc. 1974, 96, 590-591.
13. For an overview of aryl methyl ether cleavage with thiolates, see: Merriman, G. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 5, pp 3161-3163.
14. For general experimental procedures see the Supporting Information in: Kelly, T. R.; Silva, R. A.; De Silva, H.; Jasmin, S.; Zhao, Y. J. Am. Chem. Soc. 2000, 122, 6935-6949.
15. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904.