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Total synthesis of calystegine B4

Journal Article


Abstract


  • The total synthesis of calystegine B4 was achieved in 10 steps from (-)-D-lyxose by using a new synthetic strategy to obtain the requisite protected hydroxylated 4-aminocyclohept-2-en1-one without the problem of regioisomer formation that was a problem in the earlier synthesis of this natural product. The key steps included a Petasis-borono-Mannich reaction and a ring-closing metathesis reaction. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

UOW Authors


  •   Moosophon, Panawan (external author)
  •   Baird, Morwenna C. (external author)
  •   Kanokmedhakul, Somdej (external author)
  •   Pyne, Stephen

Publication Date


  • 2010

Citation


  • Moosophon, P., Baird, M. C., Kanokmedhakul, S. & Pyne, S. G. (2010). Total synthesis of calystegine B4. European Journal of Organic Chemistry, 2010 (17), 3337-3344.

Scopus Eid


  • 2-s2.0-77952968053

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4574

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3337

End Page


  • 3344

Volume


  • 2010

Issue


  • 17

Abstract


  • The total synthesis of calystegine B4 was achieved in 10 steps from (-)-D-lyxose by using a new synthetic strategy to obtain the requisite protected hydroxylated 4-aminocyclohept-2-en1-one without the problem of regioisomer formation that was a problem in the earlier synthesis of this natural product. The key steps included a Petasis-borono-Mannich reaction and a ring-closing metathesis reaction. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

UOW Authors


  •   Moosophon, Panawan (external author)
  •   Baird, Morwenna C. (external author)
  •   Kanokmedhakul, Somdej (external author)
  •   Pyne, Stephen

Publication Date


  • 2010

Citation


  • Moosophon, P., Baird, M. C., Kanokmedhakul, S. & Pyne, S. G. (2010). Total synthesis of calystegine B4. European Journal of Organic Chemistry, 2010 (17), 3337-3344.

Scopus Eid


  • 2-s2.0-77952968053

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4574

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3337

End Page


  • 3344

Volume


  • 2010

Issue


  • 17