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Volumn 45, Issue 8, 1989, Pages 2431-2449

Tremorgenic indole alkaloid studies. 6. Preparation of an advanced intermediate for the synthesis of penitrem D. Synthesis of an indole oxocane

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL STRUCTURE; PENITREM D; SYNTHESIS;

EID: 0024518004     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)83440-2     Document Type: Article
Times cited : (28)

References (92)
  • 1
    • 84918123770 scopus 로고    scopus 로고
    • Taken in part from the doctoral dissertation of J. N. Haseltine, University of Pennsylvania, 1988.
  • 10
    • 0008892388 scopus 로고
    • Penicillium crustosum and P. simplicissimum, the Correct Names for Two Common Species Producing Tremorgenic Mycotoxins
    • (1979) Mycologia , vol.71 , pp. 1166-1177
    • Pitt1
  • 36
    • 84918123766 scopus 로고    scopus 로고
    • We thank Professor W. Clark Still for a copy of Macromodel.
  • 37
    • 0002062240 scopus 로고
    • The Robinson Annelation and Related Reactions
    • For a review of the Robinson annulation, see
    • (1976) Synthesis , pp. 777-794
    • Gawley1
  • 41
    • 0000157655 scopus 로고
    • For reviews on the synthetic utility of the [2+2]-photocycloadditon, see, A. Padwa, Marcel Dekker, New York
    • (1981) Organic Photochemistry , vol.5 , pp. 123-225
    • Baldwin1
  • 43
    • 84918123765 scopus 로고    scopus 로고
    • Details concerning the Eastern Hemisphere will be reported in due course.
  • 44
    • 84918123764 scopus 로고    scopus 로고
    • Haseltine, J.; Visnick, M.; Smith, III, A.B. J. Am. Chem Soc. (submitted for publication).
  • 48
    • 0001491964 scopus 로고
    • A resolution of 6-benzyloxymethyl-3-methoxy-2-cyclohexen-1-one has been achieved via the Johnson sulfoximine protocol
    • (1984) Tetrahedron , vol.40 , pp. 1225-1233
    • Johnson1    Zeller2
  • 49
    • 84986438464 scopus 로고
    • Amberlyst-15, a Superior Catalyst for the Preparation of Enol Ethers and Acetals
    • (1974) Synthesis , pp. 348-349
    • Patwardhan1    Dev2
  • 52
    • 84918123763 scopus 로고    scopus 로고
    • Unpublished results of Dr. P. Carroll, University of Pennsylvania X-Ray Crystallographic Facility.
  • 63
    • 84918123762 scopus 로고    scopus 로고
    • Personal communication from Professor A.I. Meyers, Colorado State University.
  • 64
    • 84918123761 scopus 로고    scopus 로고
    • Deuteration of the lithium dianion of N-TMS-26 led to a 75% recovery of 26, of which approximately 52-57% displayed D-incorporation at the o-methyl group (by 1H NMR integration and mass spectral analysis). This indicates, as does the 75% recovery, that the unusually low yield of indole 27 results from shortcomings of the metallation rather than the quenching step.
  • 70
    • 33947332005 scopus 로고
    • For discussions of hard/soft acid and base theory as it applies to other ambident nucleophiles, see
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1827-1836
    • Pearson1    Songstad2
  • 74
    • 84986438464 scopus 로고
    • Amberlyst-15, a Superior Catalyst for the Preparation of Enol Ethers and Acetals
    • Prepared from commercially available 2,4-dimethoxybenzaldehyde (Aldrich) according to the general method of S. Dev; see reference 19.
    • (1974) Synthesis , pp. 348-349
    • Patwardhan1    Dev2
  • 89
    • 84918123760 scopus 로고    scopus 로고
    • Unpublished results of John Haseltine, University of Pennsylvania.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.