meta-selective aromatic borylation as key step in the synthesis of poipuol

Synthesis

Volumn , Issue 14 SPEC. ISS., 2008, Pages 2217-2220

  Cordes, Jens ^a   Wessel, Claas ^a   Harms, Klaus ^a   Koert, Ulrich ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Boron; Iridium; meta selective aromatic substitution; Natural products; Total synthesis

Indexed keywords

AROMATIC COMPOUNDS; ESTERS; IRIDIUM; ORGANIC COMPOUNDS; RAW MATERIALS;

BORON; BORYLATION; MARINE NATURAL PRODUCTS; META-SELECTIVE AROMATIC SUBSTITUTION; NATURAL PRODUCTS; REACTION SEQUENCES; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

BORON; IRIDIUM; NATURAL PRODUCT; POIPUOL;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYRTIOS; MARINE SPECIES; SYNTHESIS; X RAY ANALYSIS;

EID: 48549094170     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078449     Document Type: Article

References (12)

1. (a) Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem. Int. Ed. 2002, 41, 3056.
2. (b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
3. (c) Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E. Jr.; Smith, M. R. III. Science 2002, 295, 305.
4. (d) Maleczka, R. E. Jr.; Shi, F.; Homes, D.; Smith, M. R. III. J. Am. Chem. Soc. 2003, 125, 7792.
5. (e) Mkhalid, I. A. I.; Coventry, D. N.; Albesa-Jove, D.; Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew. Chem. Int. Ed. 2006, 45, 489.
6. Sata, N.; Galario, M. A.; Sitachitta, N.; Scheuer, P. J.; Kelly, M. J. Nat. Prod. 2005, 68, 262.
7. Antonioletti, R.; Bovicelli, P.; Malancona, S. Tetrahedron 2002, 58, 589.
8. Bliese, R. R.; McElvain, S. M. J. Am. Chem. Soc. 1933, 1697.
9. Kabalka, G. W.; Akula, M. R.; Huffman, J. W. Synthesis 2005, 547.
10. Roedig, A.; Ganns, E. M.; Henrich, C.; Schnutenhaus, H. Liebigs Ann. Chem. 1981, 1674.
11. int = 0.0775), R1 = 0.0339, wR2 = 0.0709 (all data).
12. Haight, A. R.; Bailey, A. E.; Baker, W. S.; Cain, M. H.; Copp, R. R.; DeMattei, J. A.; Ford, K. L.; Henry, R. F.; Oliver, P. A.; Parekh, S. I.; Patel, H. H.; Seif, L. S.; Staeger, M. A.; Wayne, G. S.; Wittenberger, S. J.; Zhang, W. Org. Process Res. Dev. 2004, 8, 897.