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Volumn 45, Issue 43, 2006, Pages 7199-7202

The changing faces of halogenated marine natural products: Total synthesis of the reported structures of elatenyne and an enyne from Laurencia majuscula

Author keywords

Fused ring systems; Natural products; Revised structures; Structure elucidation; Total synthesis

Indexed keywords

NITROGEN COMPOUNDS; OCEAN STRUCTURES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33751003265     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602211     Document Type: Article
Times cited : (59)

References (38)
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    • The bis(lactone) 5 has been synthesized in two steps from commercially available materials: M. E. Maier, S. Reuter, Synlett 1995, 1029.
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  • 15
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    • note
    • The anomeric acetates 6 gave the pyrano[3,2-b]pyran 8 in low yield on treatment with iodotrimethylsilane in acetonitrile.
  • 17
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    • note
    • The asymmetric diol was inseparable at this stage and was removed after ozonolysis of 11.
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    • note
    • [8].
  • 20
    • 0001653177 scopus 로고
    • Solvent effects in the reduction of halides and tosylates: S. Krishnamurthy, J. Org. Chem. 1980, 45, 2550.
    • (1980) J. Org. Chem. , vol.45 , pp. 2550
    • Krishnamurthy, S.1
  • 24
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    • Bromination of the bis(triflate) 20 cannot occur from the ground state, O-inside conformation, and will be further slowed by the β-oxygen effect, see: S. S. Shaik, J. Am. Chem. Soc. 1983, 105, 4359.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 4359
    • Shaik, S.S.1
  • 25
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    • For discussion of the conformational preferences of pyrano[3,2-b]pyrans and related systems, see: R. W. Hoffmann, I. Münster, Ann. Chem. 1997, 1143;
    • (1997) Ann. Chem. , pp. 1143
    • Hoffmann, R.W.1    Münster, I.2
  • 28
    • 33750974706 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the dibromide was established by analysis of the coupling constants (see the Supporting Information).
  • 29
    • 33751006676 scopus 로고    scopus 로고
    • note
    • The diol 10 contained an inseparable impurity which was removed after chlorination of 23.
  • 30
    • 33750971391 scopus 로고    scopus 로고
    • note
    • 1H NMR COSY experiments. The origin of the regioselectivity of the Wittig reaction may be steric in nature because of the larger size of an OTES group with respect to a chlorine atom.
  • 32
    • 33750984463 scopus 로고    scopus 로고
    • note
    • The enyne 4 was isolated as an inseparable 8:1 mixture of E and Z isomers.
  • 33
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    • For an excellent review regarding recent misassigned natural products, see: K. C. Nicolaou, S. A. Snyder, Angew. Chem. 2005, 117, 2086;
    • (2005) Angew. Chem. , vol.117 , pp. 2086
    • Nicolaou, K.C.1    Snyder, S.A.2
  • 35
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    • note
    • 13C NMR chemical shifts for 74 synthetic pyrano[3,2-b]pyran and 27 synthetic 2,2′-bifuranyl compounds.
  • 36
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    • note
    • [2].
  • 37
    • 33751008304 scopus 로고
    • PhD Thesis, La Trobe University (Australia)
    • 15 halogenated 2,2′-bifuranyl natural products had been reported. A 2,2′-bifuranyl structure for elatenyne was considered less likely than the corresponding pyrano[3,2-b]pyran: J. G. Hall, PhD Thesis, La Trobe University (Australia), 1984.
    • (1984)
    • Hall, J.G.1
  • 38
    • 33750985624 scopus 로고    scopus 로고
    • note
    • Unlike a number of pyrano[3,2-b]pyrans we synthesized, neither elatenyne nor the enyne from L. majuscula are crystalline which may be partly because of the extra degree of freedom around the central C-C bond in 2,2′-bifuranyl units.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.