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Volumn 9, Issue 20, 2003, Pages 4980-4990

Systematic Construction of a Monotetrahydrofuran-Ring Library in Annonaceous Acetogenins by Asymmetric Alkynylation and Stereodivergent Tetrahydrofuran-Ring Formation

Author keywords

Alkynylations; Cyclization; Polyketides; Stereodivergent synthesis; Synthetic methods

Indexed keywords

ALKYLATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0142259967     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305185     Document Type: Article
Times cited : (45)

References (65)
  • 6
    • 0001439593 scopus 로고
    • Annonaceous Acetogenins
    • (Eds.: J. T. Arnason, R. Mata, J. T. Romeo), Plenum Press, New York
    • f) "Annonaceous Acetogenins": Z.-M. Gu, G.-X. Zhao, N. H. Oberlies, L. Zeng, J. L. McLaughlin, in Recent Advances in Phytochemistry, Vol. 29 (Eds.: J. T. Arnason, R. Mata, J. T. Romeo), Plenum Press, New York, 1995, pp. 249-310;
    • (1995) Recent Advances in Phytochemistry , vol.29 , pp. 249-310
    • Gu, Z.-M.1    Zhao, G.-X.2    Oberlies, N.H.3    Zeng, L.4    McLaughlin, J.L.5
  • 30
    • 0142161684 scopus 로고    scopus 로고
    • note
    • Application to bis-THF-ring cores has already been communicated, see ref. [7a].
  • 37
    • 0142254773 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral data of the syn adducts appeared upfield by 0.1-0.2 ppm relative to those in the spectra of the anti adducts. On the other hand, the signals of the OH protons in the syn adducts appeared downfield by 0.1-0.2 ppm relative to those in the anti adducts. The shifts were consistent for each compound in this series.
  • 38
    • 0142254774 scopus 로고    scopus 로고
    • note
    • We found that a combination of the aldehyde (S)-6 with (1S&2R)-NME provided better selectivity than the corresponding combination of (S)-6 with (1R,2S)-NME. Carreira and co-workers also reported similar results in the asymmetric alkynylation of (S)-6 with acetyl propargyl alcohol,[8a] but the reaction mechanism was not mentioned.
  • 40
    • 0028841840 scopus 로고
    • Other synthetic procedures for 3-butyne-12-diol 13 were reported. See: b) O. Yamada, K. Ogasawara, Synthesis 1995, 1291-1294;
    • (1995) Synthesis , pp. 1291-1294
    • Yamada, O.1    Ogasawara, K.2
  • 44
    • 0034700685 scopus 로고    scopus 로고
    • During the course of our study, Pietruszka reported another solution employing the Bestmann-Ohira reagent for alkyne 13. See: J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293-4300.
    • (2000) J. Chem. Soc. Perkin Trans. 1 , pp. 4293-4300
    • Pietruszka, J.1    Witt, A.2
  • 45
    • 0142223663 scopus 로고    scopus 로고
    • note
    • Koert reported a similar double stereodifferentiation in the substrate-controlled addition of α-tetrahydrofuranic aldehyde with the chiral 3,4-isopropylidenedioxybutyl anion.[6b]
  • 49
    • 0142192566 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of related compounds. The details are described in ref. [13].
  • 54
    • 0142192565 scopus 로고    scopus 로고
    • note
    • 2 was dried before use.[8d] We found that this protocol is very effective for obtaining reproducibility of the yield. Therefore, the modified procedure was employed after this entry.
  • 55
    • 0142161680 scopus 로고    scopus 로고
    • note
    • Carreira and co-workers reported a catalytic version of the asymmetric alkynylation.[8b] We examined the asymmetric alkynylation of the aldehyde 20 with the alkyne 25 under the catalytic conditions but the reaction did not proceed.
  • 56
    • 0142254772 scopus 로고    scopus 로고
    • note
    • The diastereomeric ratio based on the benzylidene acetal for 26a and 26b was almost the same as the ratio of 25a and 25b used.
  • 59
    • 0037017721 scopus 로고    scopus 로고
    • Recently, a one-pot THF-ring formation from the 1,2,5-triol derivatives was reported by Forsyth and co-workers. See: a) A. B. Dounay, G. J. Florence, A. Saito, C. J. Forsyth, Tetrahedron 2002, 58, 1865-1874;
    • (2002) Tetrahedron , vol.58 , pp. 1865-1874
    • Dounay, A.B.1    Florence, G.J.2    Saito, A.3    Forsyth, C.J.4
  • 65
    • 0142161681 scopus 로고    scopus 로고
    • note
    • The moderate yields in some entries were caused by base-promoted deprotection of the TMS group in the coupling product and subsequent coupling of the resulting acetylide with another aldehyde.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.