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Volumn 129, Issue 8, 2007, Pages 2206-2207

Synthesis of a ring-expanded bryostatin analogue

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN; BRYOSTATIN DERIVATIVE; NATURAL PRODUCT; RUBIDIUM; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847638397     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067305j     Document Type: Article
Times cited : (90)

References (37)
  • 19
    • 33847684113 scopus 로고    scopus 로고
    • The Julia olefination, a well-established method in the previous three total syntheses for the construction of the macrocycle, is unlikely to work for our system due to the basicity of this procedure; see ref 5b
    • The Julia olefination, a well-established method in the previous three total syntheses for the construction of the macrocycle, is unlikely to work for our system due to the basicity of this procedure; see ref 5b.
  • 21
    • 33847614116 scopus 로고    scopus 로고
    • Our efforts to construct the bryostatin macrocycle via a RCM reaction met with no success; details will be reported in full account of our work. For another RCM approach by Thomas and co-workers, see ref 3f
    • Our efforts to construct the bryostatin macrocycle via a RCM reaction met with no success; details will be reported in full account of our work. For another RCM approach by Thomas and co-workers, see ref 3f.
  • 27
    • 33847634585 scopus 로고    scopus 로고
    • Synthesized in three steps from 3-methyl-2-butanone. See Supporting Information for details.
    • Synthesized in three steps from 3-methyl-2-butanone. See Supporting Information for details.
  • 28
    • 33847690065 scopus 로고    scopus 로고
    • This reaction is reproducible at 0.3 mmol scale. For large-scale reactions, a two-step procedure of Pd(OAc)2-catalyzed cross-coupling of 17 and 18 to form a ene-yne adduct followed by PdCl 2(CH3CN)2-catalyzed cycloisomerization was performed. See Supporting Information for details
    • 2-catalyzed cycloisomerization was performed. See Supporting Information for details.
  • 35
    • 4143062538 scopus 로고    scopus 로고
    • Under this and several other conditions, relay ring-closing metathesis (RRCM) did not occur. For a leading reference on RRCM, see: Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210.
    • Under this and several other conditions, relay ring-closing metathesis (RRCM) did not occur. For a leading reference on RRCM, see: Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210.
  • 36
    • 33746581932 scopus 로고    scopus 로고
    • 50 values of 10 and 240 nM, respectively, in the same assay; see: (a) Hearn, B. R.; Zhang, D.; Li, Y.; Myles, D. C. Org. Lett. 2006, 8, 3057.
    • 50 values of 10 and 240 nM, respectively, in the same assay; see: (a) Hearn, B. R.; Zhang, D.; Li, Y.; Myles, D. C. Org. Lett. 2006, 8, 3057.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.