메뉴 건너뛰기




Volumn 10, Issue 7, 2008, Pages 1421-1424

A multifaceted phosphate tether: Application to the C15-C30 subunit of dolabelides A-D

Author keywords

[No Author keywords available]

Indexed keywords

DOLABELIDE A; DOLABELIDE B; DOLABELIDE C; DOLABELIDE D; MACROLIDE; ORGANOPHOSPHORUS COMPOUND;

EID: 45849083536     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8001865     Document Type: Article
Times cited : (23)

References (36)
  • 15
    • 4444282084 scopus 로고    scopus 로고
    • Burke and coworkers have shown this protocol to be compatible with multiple acetate protecting groups; see: Lucas, B. S, Luther, L. M, Burke, S. D. Org. Lett. 2004, 6, 2965-2968
    • Burke and coworkers have shown this protocol to be compatible with multiple acetate protecting groups; see: Lucas, B. S.; Luther, L. M.; Burke, S. D. Org. Lett. 2004, 6, 2965-2968.
  • 16
    • 59849106162 scopus 로고    scopus 로고
    • This reaction occurs via a highly regio- and stereoselective anti-SN2′ attack at the C(22) olefinic carbon within bicyclic phosphate 7 where proper orthogonal alignment of the C=Cπ* and C-OP(O)σ* orbitals allows for anti-S N2′ attack to proceed exclusively on the convex face of 7; see Scheme 4 in ref 5a
    • N2′ attack to proceed exclusively on the convex face of 7; see Scheme 4 in ref 5a.
  • 17
    • 23944510563 scopus 로고    scopus 로고
    • For selective silylation of similar 1,3-diols, see: a
    • For selective silylation of similar 1,3-diols, see: (a) Soltani, O.; De Brabander, J. K. Org. Lett. 2005, 7, 2791-2793.
    • (2005) Org. Lett , vol.7 , pp. 2791-2793
    • Soltani, O.1    De Brabander, J.K.2
  • 24
    • 0001213599 scopus 로고    scopus 로고
    • These results are in accordance with literature precedence that larger counterions effect the Felkin selectivity; see: Mengel, A, Reiser, O. Chem. Rev. 1999, 99, 1191-1223
    • These results are in accordance with literature precedence that larger counterions effect the Felkin selectivity; see: Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223.
  • 27
    • 38349121101 scopus 로고    scopus 로고
    • Marshall and coworkers reported protonolysis products under Oppolzer conditions with similar homoallylic protected vinyl iodides, which we witnessed in unsuccessful reactions, along with decomposed aldehyde; see: Marshall, J. A, Eidam, P. M. Org. Lett. 2008, 10, 93-96
    • Marshall and coworkers reported protonolysis products under Oppolzer conditions with similar homoallylic protected vinyl iodides, which we witnessed in unsuccessful reactions, along with decomposed aldehyde; see: Marshall, J. A.; Eidam, P. M. Org. Lett. 2008, 10, 93-96.
  • 30
    • 0027729991 scopus 로고    scopus 로고
    • 4) failed to generate the desired C23 stereochemistry. (a) Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 115, 11446-59.
    • 4) failed to generate the desired C23 stereochemistry. (a) Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 115, 11446-59.
  • 33
    • 0034734340 scopus 로고    scopus 로고
    • Second generation Hoveyda-Grubbs catalyst: Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
    • Second generation Hoveyda-Grubbs catalyst: Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
  • 35
    • 0037118313 scopus 로고    scopus 로고
    • For examples of diimide reductions in synthesis, see: (a) Haukaas, M. H, O'Doherty, G. A. Org. Lett. 2002, 4, 1771-1774
    • For examples of diimide reductions in synthesis, see: (a) Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771-1774.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.