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Volumn 48, Issue 46, 2009, Pages 8780-8783

Syntheses and biological evaluation of iriomoteolide 3a and analogues

Author keywords

Anticancer agents; Macrocycles; Metathesis; Natural products; Total synthesis

Indexed keywords

ANTICANCER AGENTS; MACROCYCLES; METATHESIS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 70350578520     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903379     Document Type: Article
Times cited : (31)

References (47)
  • 3
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    • Leading references for the total synthesis of amphidinolides: Amphidinolide A
    • Leading references for the total synthesis of amphidinolides: Amphidinolide A:
  • 10
    • 37349016936 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 9265-9270;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 9265-9270
  • 14
    • 0037122052 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 4763-4766;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4763-4766
  • 16
    • 34547235970 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5545-5548.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5545-5548
  • 18
    • 58149159438 scopus 로고    scopus 로고
    • Progress towards the total synthesis of iriomoteolide-la: b) L. Fang, H. Xue, J. Yang, Org. Lett. 2008, 10, 4645-4648;
    • (2008) Org. Lett. , vol.10 , pp. 4645-4648
    • Fang, L.1    Xue, H.2    Yang, J.3
  • 26
    • 70350601582 scopus 로고    scopus 로고
    • Alternative synthesis of compound 9 starting with a TBSprotected alkyl iodide (8') gave lower yields and poor diastereomeric ratios. The TBDPS to TBS swap was necessary to allow further functional group manipulations at a later stage of the synthesis
    • Alternative synthesis of compound 9 starting with a TBSprotected alkyl iodide (8') gave lower yields and poor diastereomeric ratios. The TBDPS to TBS swap was necessary to allow further functional group manipulations at a later stage of the synthesis.
  • 32
    • 70350598684 scopus 로고    scopus 로고
    • Benzyl ether removal in presence of the free acid, even under neutral conditions, led to partial lactonization of the resulting alcohol
    • Benzyl ether removal in presence of the free acid, even under neutral conditions, led to partial lactonization of the resulting alcohol.
  • 35
    • 85027732552 scopus 로고    scopus 로고
    • For the formation of the diol 5a, see a
    • For the formation of the diol 5a, see a) M. A. Robbins, P. N. Devine, T. Oh, Org. Synth. 1999, 76, 101-109;
    • (1999) Org. Synth. , vol.76 , pp. 101-109
    • Robbins, M.A.1    Devine, P.N.2    Oh, T.3
  • 39
    • 70350577877 scopus 로고    scopus 로고
    • For further details, see the Supporting Information
    • For further details, see the Supporting Information.
  • 40
    • 28844501313 scopus 로고    scopus 로고
    • and references therein
    • See reference [16c] and also: S. Michaelis, M. Blechert, Org. Lett. 2005, 7, 5513-5516, and references therein.
    • (2005) Org. Lett. , vol.7 , pp. 5513-5516
    • Michaelis, S.1    Blechert, M.2
  • 41
    • 70350611908 scopus 로고    scopus 로고
    • Compounds 22a and 22b could be separated at this stage to give a 2:1 ratio, confirming the E configuration of the olefin produced in the CM event
    • Compounds 22a and 22b could be separated at this stage to give a 2:1 ratio, confirming the E configuration of the olefin produced in the CM event.
  • 42
    • 33847081223 scopus 로고    scopus 로고
    • A single successful precedent for such transformation is reported using TASF: R. Lira, W. R. Roush, Org. Lett. 2007, 9, 533-536.
    • (2007) Org. Lett. , vol.9 , pp. 533-536
    • Lira, R.1    Roush, W.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.