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Volumn 37, Issue 1-2, 1998, Pages 190-196

Total Synthesis of Altohyrtin A (Spongistatin 1): Part 2

Author keywords

Altohyrtin; Antitumor agents; Natural products; Spongistatin; Total synthesis

Indexed keywords


EID: 0031951004     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.0.co;2-0     Document Type: Article
Times cited : (107)

References (40)
  • 2
    • 0031906655 scopus 로고    scopus 로고
    • J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, and Y. Kishi, Angew. Chem. 1998, 109, 198-20; Angew. Chem. Int. Ed. Engl. 1998, 37, 187-192.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 187-192
  • 8
    • 85088077132 scopus 로고    scopus 로고
    • 1C NMR, MS, and others) were obtained for all new compounds
    • 1C NMR, MS, and others) were obtained for all new compounds.
  • 9
    • 0346763729 scopus 로고    scopus 로고
    • For abbreviations used, see reference 14 in ref. [1] (preceding communication)
    • For abbreviations used, see reference 14 in ref. [1] (preceding communication).
  • 12
    • 0348024884 scopus 로고    scopus 로고
    • note
    • The allylstannane was also prepared by an alternative synthetic route: addition of the 1,3-dithiane anion to TBS-glycidol, followed by cleavage of the TBS protecting group and acetonide formation, yielded the functionalized 1,3-dithiane, which was further lithiated and trapped with DMF. Reduction of the resultant aldehyde, followed by TBS-protection. dithiane deprutection. Wittig-olefination, and TBS- deprotection, gave an allyl alcohol, which was converted into 18 by adopting the last two reactions of step g in Scheme 2).
  • 17
    • 0030979761 scopus 로고    scopus 로고
    • Example of 2,3-dihalopropenes used in organoindium reactions: X.-H. Yi, Y. Meng, C.-J. Li, Tetrahedron Lett. 1997, 38, 4731-4734.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4731-4734
    • Yi, X.-H.1    Meng, Y.2    Li, C.-J.3
  • 19
    • 85088076454 scopus 로고    scopus 로고
    • note
    • II-mediated couplings of iodoglucals with aldehydes proceeded smoothly to yield a diastereomeric mixture of allylic alcohols: the major product was the undesired stereoisomer. Second, addition of the 1,3-dithiane anion (THF, HMPA) of an acyclic E-ring precursor to a model aldehyde gave the undesired diastereomer as the major product.
  • 20
    • 85088076139 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude product showed the stereoselectivity of this coupling to he greater than 7:1. The minor undesired C38 diastereomer could he converted stereospecifically into the desired isomer by oxidation with TPAP/NMO followed by Luche reduction.
  • 23
    • 0346133231 scopus 로고    scopus 로고
    • note
    • The chemical shift differences of the (S)- and (R)-Mosher esters at C38 were positive for the C33-C36 region and negative for the C39-C51 region, demonstrating the desired absolute configuration at C38.
  • 24
    • 0348024883 scopus 로고    scopus 로고
    • note
    • Preliminary studies on deprotection of silyl-protected altohyrtin A demonstrated that removal of the C35 TIPS group required prolonged and detrimental exposure to HF · py (5days).
  • 28
    • 0348024882 scopus 로고    scopus 로고
    • COSY experiments demonstrated exclusive acylation of the C41 alcohol
    • COSY experiments demonstrated exclusive acylation of the C41 alcohol.
  • 29
    • 0346133229 scopus 로고    scopus 로고
    • While conversion of the C37 methyl ketal in the C37 lactol should be facile, this has not been tested experimentally
    • While conversion of the C37 methyl ketal in the C37 lactol should be facile, this has not been tested experimentally.
  • 30
    • 0347394108 scopus 로고    scopus 로고
    • note
    • The deproteclion under the specified condition in Scheme 4 was very clean (TLC analysis), hut the yield of the isolated product was only in the ranee of 20-30%. It is not yet established whether this low yield is due to a problem with isolation and/or with unidentified decomposition/side-reaclions.
  • 31
    • 0346133226 scopus 로고    scopus 로고
    • The bioassays were performed by Dr. Bruce Littlefield at Eisai Research Institute, Andover, Massachussetts
    • The bioassays were performed by Dr. Bruce Littlefield at Eisai Research Institute, Andover, Massachussetts.
  • 32
    • 0346133230 scopus 로고    scopus 로고
    • note
    • The cytotoxicity was tested against DLD-1 human colon cancer, U937 human histiocytic lymphoma, and LOX human melanoma cells. Details of these experiments shall be reported elsewhere.
  • 35
    • 0032491845 scopus 로고    scopus 로고
    • Through the total synthesis of altohyrtin C (spongistatin 2), Evans has reached the same conclusion: D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2744-2747
  • 36
    • 0347394107 scopus 로고    scopus 로고
    • The sulfone was derived from the addition of sodium benzene sulfinate to the TIPS ether of 3-bromo-1-propanol
    • The sulfone was derived from the addition of sodium benzene sulfinate to the TIPS ether of 3-bromo-1-propanol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.