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Volumn 7, Issue 15, 2005, Pages 3231-3234

Synthesis and [4 + 2]-annulation of enantioenriched (Z)-crotylsilanes: Preparation of the C1-C13 fragment of bistramide A

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; BISTRATENE A; PYRAN DERIVATIVE; SILANE DERIVATIVE; SPIRO COMPOUND;

EID: 23044445819     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050982i     Document Type: Article
Times cited : (47)

References (51)
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    • Marcel Dekker: New York
    • (e) Westly, J. W., Ed. Polyether Antibiotics; Marcel Dekker: New York, 1983; Vols. I and II.
    • (1983) Polyether Antibiotics , vol.1-2
    • Westly, J.W.1
  • 24
    • 23044487960 scopus 로고    scopus 로고
    • note
    • Vinylsilane 9 may be prepared in three steps from commercially available propargyl alcohol. See the Supporting Information.
  • 25
    • 23044466384 scopus 로고    scopus 로고
    • note
    • Lipase PS-D "Amano" I from Lot No. ILPSAY0352205K may be purchased from Amano Enzyme USA Co., Lomdard, IL 60148.
  • 26
    • 23044509425 scopus 로고    scopus 로고
    • note
    • The free alcohol of 10 was obtained in 94% yield (two steps from the racemic epoxide) and found to have 94-96% ee. Alcohol 11 was obtained in 89% yield and 94-97% ee.
  • 31
    • 23044516926 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for experimental details.
  • 32
    • 23044472268 scopus 로고    scopus 로고
    • note
    • Minor amounts of side products of the reaction include homo-aldol coupling followed by dehydration and Peterson olefination to give the conjugated esters of 3 and 4.
  • 33
    • 23044512856 scopus 로고    scopus 로고
    • Ph.D. Thesis, Boston University
    • For an interpretation of the stereochemical course of (E)-crotylsilanes in the [4 + 2]-annulations, see: Huang, H. Ph.D. Thesis, Boston University, 2005.
    • (2005)
    • Huang, H.1
  • 34
    • 23044465940 scopus 로고    scopus 로고
    • note
    • Enantiomeric excess (ee) analysis was preformed using chiral HPLC analysis with a CHIRALCEL OD column. See the Supporting Information.
  • 35
    • 2742569677 scopus 로고
    • It has been suggested that silicon prefers an axial orientation for both electronic and steric reasons but may still eliminate even without optimal orbital overlap. For a detailed discussion and relevant examples, see: Lambert, J. B. Tetrahedron 1990, 46, 2677.
    • (1990) Tetrahedron , vol.46 , pp. 2677
    • Lambert, J.B.1
  • 37
    • 0034966749 scopus 로고    scopus 로고
    • It is conceivable that an oxonia-Cope rearrangement could play a role in the stereochemical outcome of these reactions; however, no byproducts from this pathway were observed. For an example of oxonia-Cope rearrangements in allyl systems, see: Roush, W. R.; Dilley, G. J. Synlett 2001, SI, 955.
    • (2001) Synlett , vol.SI , pp. 955
    • Roush, W.R.1    Dilley, G.J.2
  • 38
    • 23044449707 scopus 로고    scopus 로고
    • see ref 2b
    • For an example of oxonia-Cope rearrangement of ester-substituted oxycarbenium vinylsilanes to form dihydropyrans, see ref 2b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.