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Volumn 128, Issue 23, 2006, Pages 7463-7465

Unified total synthesis of pteriatoxins and their diastereomers

Author keywords

[No Author keywords available]

Indexed keywords

NEUROTOXIN; PTERIATOXIN; UNCLASSIFIED DRUG;

EID: 33745028358     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0618954     Document Type: Article
Times cited : (58)

References (46)
  • 22
    • 33745039348 scopus 로고    scopus 로고
    • note
    • A 1:1 mixture (0.3 mg) of PnTXs B/C was isolated from 21 kg of the viscera of Pinna muricata. PtTX A (20 μg) and PtTX B/C (8 μg as a 1:1 mixture) were isolated from 82 kg of the viscera of Pteria penguin.
  • 23
    • 33745038127 scopus 로고    scopus 로고
    • note
    • 99 in ref 4: PnTXs B/C = 22 μg/kg; PtTX A = 100μg/kg; PtTXs B/C = 8 μg/kg).
  • 24
    • 33745039082 scopus 로고    scopus 로고
    • note
    • The stereochemical homogeneity of PtTX A is discussed in a subsequent paper, see ref 23.
  • 25
    • 33745017554 scopus 로고    scopus 로고
    • note
    • A total synthesis of PnTXs B and C from the Diels-Alder products 14a-iii and 14b-iii, respectively, will be reported elsewhere.
  • 26
    • 33745011732 scopus 로고    scopus 로고
    • note
    • The building blocks dithiane 1 and vinyl iodide 2 were reported in ref 3. We adopted the reported synthesis for preparation of vinyl iodide 2. However, we have made substantial modifications on the synthesis of dithiane 1; for details, see Supporting Information.
  • 30
    • 33745046964 scopus 로고    scopus 로고
    • note
    • For details, see Supporting Information.
  • 31
    • 0037486826 scopus 로고    scopus 로고
    • For selected reviews on Cr-mediated reactions, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991.
    • (1999) Chem. Rev. , vol.99 , pp. 991
    • Fürstner, A.1
  • 34
    • 0000507168 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (d) Saccomano, N. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, p 173.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 173
    • Saccomano, N.A.1
  • 35
    • 0008279260 scopus 로고    scopus 로고
    • A Ni/Cr-mediated coupling similar to the present case is known: Taylor, R. E.; Ciavarri, J. P. Org. Lett. 1999, 1, 467.
    • (1999) Org. Lett. , vol.1 , pp. 467
    • Taylor, R.E.1    Ciavarri, J.P.2
  • 36
    • 33745035323 scopus 로고    scopus 로고
    • note
    • 3, MeOH; 3, PPTS, 63% over 3 steps.
  • 37
    • 33745030678 scopus 로고    scopus 로고
    • note
    • The substrates 12 and 13 did not survive in the presence of Lewis acids or in the absence of Sumilizer.
  • 38
    • 33745056842 scopus 로고    scopus 로고
    • note
    • The intramolecular Diels-Alder reaction of 12a and 12b was not observed below the indicated temperature.
  • 42
    • 33745037356 scopus 로고    scopus 로고
    • note
    • This was evident because these stereoisomers were not detected in the corresponding C34-α series or vice versa.
  • 44
    • 33745034625 scopus 로고    scopus 로고
    • note
    • We assumed, and indeed observed, that acid-promoted deprotection of the t-Bu ester requires much more forcing conditions, once the amino-protecting group is hydrolyzed.
  • 45
    • 33745019730 scopus 로고    scopus 로고
    • note
    • 3CN = 3/1 (v/v) containing 0.1% TFA. Flow rate: 2 mL/min, isocratic. Detection: 216 nm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.