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Volumn 9, Issue 25, 2007, Pages 5299-5302

Highly functionalized pyranopyrans from furans: A synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FURAN DERIVATIVE; NORHALICHONDRIN B; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 37249004685     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702559e     Document Type: Article
Times cited : (52)

References (52)
  • 7
  • 9
    • 0000895818 scopus 로고
    • For early studies from the Kishi group, see: a
    • For early studies from the Kishi group, see: (a) Aicher, T. D.; Kishi, Y. Tetrahedron Lett. 1987, 28, 3463.
    • (1987) Tetrahedron Lett , vol.28 , pp. 3463
    • Aicher, T.D.1    Kishi, Y.2
  • 13
    • 3042637078 scopus 로고    scopus 로고
    • For recent work, see:, and references cited therein
    • For recent work, see: Namba, K.; Jun, H.-S.; Kishi, Y. J. Am. Chem. Soc. 2004, 126, 7770 and references cited therein.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 7770
    • Namba, K.1    Jun, H.-S.2    Kishi, Y.3
  • 14
    • 37249037247 scopus 로고    scopus 로고
    • Kishi, Y.; Fang, F. G.; Forsyth, C. J.; Scola, P. M.; Yoon, S. K. U.S. Patent 5338866, International Patent WO93/17650.
    • (a) Kishi, Y.; Fang, F. G.; Forsyth, C. J.; Scola, P. M.; Yoon, S. K. U.S. Patent 5338866, International Patent WO93/17650.
  • 15
    • 37249065405 scopus 로고    scopus 로고
    • See also ref 3b
    • (b) See also ref 3b.
  • 42
    • 0000444658 scopus 로고    scopus 로고
    • Readily obtained on a large scale from β-furylethanol by silylation with TBSC1 (imidazole, DMF, rt) and then DoM (n-BuLi, THF) with DMF as electrophile. See: Kolb, H. C.; Hoffmann, H. M. R. Tetrahedron 1990, 46, 5127.
    • Readily obtained on a large scale from β-furylethanol by silylation with TBSC1 (imidazole, DMF, rt) and then DoM (n-BuLi, THF) with DMF as electrophile. See: Kolb, H. C.; Hoffmann, H. M. R. Tetrahedron 1990, 46, 5127.
  • 43
    • 0001890944 scopus 로고    scopus 로고
    • For reviews of the use of the Achmatowicz reaction in the synthesis of oxygen-containing heterocycles, see: (a) Georgiadis, M. P, Albizati, K. F, Georgiadis, T. M. Org. Prep. Proced. Int. 1992, 24, 95
    • For reviews of the use of the Achmatowicz reaction in the synthesis of oxygen-containing heterocycles, see: (a) Georgiadis, M. P.; Albizati, K. F.; Georgiadis, T. M. Org. Prep. Proced. Int. 1992, 24, 95.
  • 48
    • 37249065926 scopus 로고    scopus 로고
    • To the best of our knowledge, highly diastereoselective reductions of simple pyranones of this type are without precedent. Studies to elucidate the underlying source of the remarkable diastereoselectivity of the Kishi reduction are ongoing and will be reported in due course
    • To the best of our knowledge, highly diastereoselective reductions of simple pyranones of this type are without precedent. Studies to elucidate the underlying source of the remarkable diastereoselectivity of the Kishi reduction are ongoing and will be reported in due course.
  • 52
    • 12344259557 scopus 로고    scopus 로고
    • Recent advancements from the Kishi laboratory include the ability to perform this reaction in the presence of chiral sulfonamide ligands. Reported diastereoselectivties for substrates similar to 20 are on the order of 12:1-15:1. See: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.
    • Recent advancements from the Kishi laboratory include the ability to perform this reaction in the presence of chiral sulfonamide ligands. Reported diastereoselectivties for substrates similar to 20 are on the order of 12:1-15:1. See: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.