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Volumn 37, Issue 1-2, 1998, Pages 187-190

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

Author keywords

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

Indexed keywords


EID: 0031906655     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<187::aid-anie187>3.0.co;2-d     Document Type: Article
Times cited : (134)

References (56)
  • 22
    • 0032491845 scopus 로고    scopus 로고
    • 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
  • 23
    • 0346763735 scopus 로고    scopus 로고
    • For this reason, we adopted the use of the name altohyrtin A in this paper. As discussed in the following paper, altohyrtin A is identical to spongistatin 1
    • For this reason, we adopted the use of the name altohyrtin A in this paper. As discussed in the following paper, altohyrtin A is identical to spongistatin 1.
  • 28
  • 29
    • 85087580643 scopus 로고    scopus 로고
    • 13C NMR, MS, and others) were obtained for all new compounds
    • 13C NMR, MS, and others) were obtained for all new compounds.
  • 30
    • 0348024893 scopus 로고    scopus 로고
    • note
    • 2O = para-toluenesulfonic anhydride.
  • 35
    • 0346763733 scopus 로고    scopus 로고
    • note
    • Careful planning of the protecting group sequence allowed incorporation of an acetate on both the C5 and C15 alcohols (spongistatin 1) or only on the C5 alcohol (spongistatin 4). Protection of the C9 tertiary alcohol was also possible with silyl groups.
  • 37
    • 0347394113 scopus 로고    scopus 로고
    • The cis vinyl iodide corresponding to 26 might be suitable for the following key Michael cyclization, though this was not tested
    • The cis vinyl iodide corresponding to 26 might be suitable for the following key Michael cyclization, though this was not tested.
  • 38
    • 0348024892 scopus 로고    scopus 로고
    • note
    • The yields (50% to 80%) for the hydrolysis and subsequent Michael addition depended on the protecting group arrangement. A substrate bearing TBS groups on the C5, C9, and C15 alcohols and TBDPS on the C25 alcohol gave the best result. One of the by-products isolated in the case of 27 was the α,β-unsaturated ketone resulting from elimination of the C15 acetate.
  • 39
    • 0346133241 scopus 로고    scopus 로고
    • These experiments were performed by Dr. Yuan Wang at Eisai Research Institute, Andover, Massachusetts
    • These experiments were performed by Dr. Yuan Wang at Eisai Research Institute, Andover, Massachusetts.
  • 40
    • 0346133240 scopus 로고    scopus 로고
    • note
    • For the C1 TBS ether of 28, distinct NOEs between the C19 and C21 protons and between the C27 and C22(eq) protons were observed. For the C1 TBS ether of 31, distinct NOEs between the C19 and C21 protons and between the C19 and C24(eq) protons were observed.
  • 44
    • 0348024891 scopus 로고    scopus 로고
    • The Wittig reaction was also studied with the aldehyde bearing the unprotected carboxylic acid at C1; the olefination did yield the desired product but in much poorer yield
    • The Wittig reaction was also studied with the aldehyde bearing the unprotected carboxylic acid at C1; the olefination did yield the desired product but in much poorer yield.
  • 46
    • 85087580920 scopus 로고    scopus 로고
    • note
    • 6]DMSO), whereas those in the C23 epimer were at δ= 5.80 and 5.37.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.