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Volumn 50, Issue 37, 2011, Pages 8629-8633

Total syntheses of heimiol A, hopeahainol D, and constrained analogues

Author keywords

cascade reactions; heterocycles; natural products; polyphenols; total synthesis

Indexed keywords

CASCADE REACTIONS; HETEROCYCLES; NATURAL PRODUCTS; POLYPHENOLS; TOTAL SYNTHESIS;

EID: 80052500559     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103575     Document Type: Article
Times cited : (54)

References (37)
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    • Using thermodynamic strain energy to dictate synthetic planning is rare, though kinetic energies have been used to great effect with one example being calculation of atropisomeric equilibrations to determine the ordering of bond constructions for the vancomycin aglycon
    • Using thermodynamic strain energy to dictate synthetic planning is rare, though kinetic energies have been used to great effect with one example being calculation of atropisomeric equilibrations to determine the ordering of bond constructions for the vancomycin aglycon:, D. L. Boger, S. Miyazaki, S. H. Kim, J. H. Wu, S. L. Castle, O. Loiseleur, Q. Jin, J. Am. Chem. Soc. 1999, 121, 10004-10011.
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    • Boger, D.L.1    Miyazaki, S.2    Kim, S.H.3    Wu, J.H.4    Castle, S.L.5    Loiseleur, O.6    Jin, Q.7
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    • Intriguingly, use of either of these reagents separately did not afford the desired product
    • Intriguingly, use of either of these reagents separately did not afford the desired product.
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    • It is worth noting that if 17 was first added to aldehyde 14, no attempt at subsequent haloetherification to reach 20 directly succeeded in any observable yield (although at best only 50 % of material could be advanced to the desired product due to the extra stereogenic center)
    • It is worth noting that if 17 was first added to aldehyde 14, no attempt at subsequent haloetherification to reach 20 directly succeeded in any observable yield (although at best only 50 % of material could be advanced to the desired product due to the extra stereogenic center).
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    • Earlier protection of the phenols as benzyl ethers prevented the smooth preparation of alcohol 13 because of issues of additional strain imparted by these groups in forging critical C-C bonds
    • Earlier protection of the phenols as benzyl ethers prevented the smooth preparation of alcohol 13 because of issues of additional strain imparted by these groups in forging critical C-C bonds.
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    • Conditions attempted included exposure to acid and heat, as well as the trityl cation to try and establish a dynamic equilibrium
    • Conditions attempted included exposure to acid and heat, as well as the trityl cation to try and establish a dynamic equilibrium.
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    • For an excellent review on synthetic approaches to polyphenolic natural products in general
    • K. C. Nicolaou, Q. Kang, T. R. Wu, C. S. Lim, D. Y.-K. Chen, J. Am. Chem. Soc. 2010, 132, 7540-7548. For an excellent review on synthetic approaches to polyphenolic natural products in general, see
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    • Nicolaou, K.C.1    Kang, Q.2    Wu, T.R.3    Lim, C.S.4    Chen, D.Y.-K.5
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    • For recent work to prepare oligomeric polyphenols beyond the dimer level
    • Angew. Chem. Int. Ed. 2011, 50, 586-621. For recent work to prepare oligomeric polyphenols beyond the dimer level, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.