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Volumn 43, Issue 15, 1987, Pages 3309-3362

Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products

Author keywords

[No Author keywords available]

Indexed keywords


EID: 15844366864     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)81626-4     Document Type: Article
Times cited : (798)

References (145)
  • 8
    • 84918152907 scopus 로고    scopus 로고
    • H.G. Hanley and J.D. Slack, Ref. 4, Ch. 8
  • 9
    • 84918152906 scopus 로고    scopus 로고
    • P.W. Reed and G. M. Bokoch, Ref. 4, Ch. 9
  • 10
    • 84918152905 scopus 로고    scopus 로고
    • M.W. Osborne, J. Wenger, M. Zanko, F. Kovzelove and M.R. Cohen, Ref. 4, Ch. 10.
  • 30
    • 0000178470 scopus 로고
    • Synthesis of Reduced Furans and 3(2H)-Dihydrofuranones with Manipulable Functionality
    • (1980) HETEROCYCLES , vol.14 , pp. 1825
    • Semple1    Joullié2
  • 37
    • 0001384079 scopus 로고
    • Oxidation of olefins by potassium permanganate. Oxygen-labeling experiments and mechanism of the oxidation of 1,5-hexadiene. Evidence for a manganese intermediate with coordination number greater than four
    • (1981) Journal of the American Chemical Society , vol.193 , pp. 940
    • Wolfe1    Ingold2
  • 46
    • 84986943610 scopus 로고
    • The Oxidation of Alcohols Using 2,2′-Bipyridinium Chlorochromate
    • (1980) Synthesis , vol.9 , pp. 691
    • Guziec1    Luzzio2
  • 55
    • 84918152904 scopus 로고    scopus 로고
    • The authors do not state whether racemic or optically pure compounds were employed.
  • 59
    • 84918152903 scopus 로고    scopus 로고
    • Preparation of 52: The ratio of 52 and its isomer by this method was at least 10:1 (97% yield). Optical resolution of 52 was achieved by preparative HLC separation of the l-a- methylbenzylurethane derivative.
  • 65
    • 84918152902 scopus 로고    scopus 로고
    • In addition, the authors have examined other examples in Ref. 39.
  • 71
    • 84918152901 scopus 로고    scopus 로고
    • The reactions were performed by adding lithium t-octyl-t-butylamide (LOBA) to the ketone and a 10-fold excess of TMSC1 in 23% HMPA/THF at -78°C. The occurrence of some equilibration prior to trapping is possible, however. The preferred mode of addition (ketone added to LOBA and TMSC1) was not feasible since LOBA reacts with TMSC1 at -78°C in the presence of HMPA.
  • 72
    • 84918152900 scopus 로고    scopus 로고
    • Addition of the trapping agent after addition of the base to the ketone.
  • 84
    • 77954924485 scopus 로고
    • Synthesis of Substituted Tetrahydrofurans and Tetrahydropyrans 1. Oxidative Cyclization of p-Methoxystyrene Derivatives with DDQ
    • (1985) HETEROCYCLES , vol.23 , pp. 553
    • Oikawa1    Horita2    Yonemitsu3
  • 90
    • 0343324714 scopus 로고
    • Studies toward polyether antibiotics: stereospecific synthesis of polysubstituted tetrahydropyrans
    • (1982) Canadian Journal of Chemistry , vol.60 , pp. 90
    • Ho1
  • 92
    • 0000455168 scopus 로고
    • Chelation-controlled nucleophilic additions. 1. A highly effective system for asymmetric induction in the reaction of organometallics with α-alkoxyketones.
    • (1980) Tetrahedron Letters , vol.21 , pp. 1031
    • Still1    McDonald2
  • 94
    • 0003905731 scopus 로고
    • For a review of the aldol reaction, see, J.D. Morrison, Academic Press, Orlando, Florida, Ch. 2.
    • (1984) Asymmetric Synthesis , vol.3
    • Heathcock1
  • 96
    • 84918152899 scopus 로고    scopus 로고
    • For synthesis of 154 see Scheme 28 and Ref. 9a
  • 97
    • 84918152898 scopus 로고    scopus 로고
    • 153 was prepared by the method of Ref. 9o.
  • 101
    • 84918152897 scopus 로고    scopus 로고
    • For synthesis of 168 see Scheme 27, Section 3.2, and synthesis of 169, see Ref. 10a.
  • 103
    • 84918152896 scopus 로고    scopus 로고
    • That is, in conformer A, 2 oxygens have an electron pair antiperiplanar to the C-O bond, while there is only one such oxygen in conformer B and none in conformer C. Therefore, A has two anomeric effects, B has one, and C has none.68
  • 131
    • 0001642353 scopus 로고
    • A Simple Route to Spiroketals via Alkylation of Dihydropyran
    • (1984) HETEROCYCLES , vol.22 , pp. 1489
    • Amoureux1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.