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Total synthesis of hyacinthacines B3, B4, and B 5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common precursor

Journal Article


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Abstract


  • The total synthesis of hyacinthacines B3, B4, and B5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common anti-1,2-amino alcohol precursor is described. These syntheses confirmed that the proposed structures and absolute configurations of hyacinthacines B3, B4, and B5 were correct and disclosed that the proposed structure of hyacinthacine B7 was incorrect. Our synthetic and spectroscopic studies suggest that the natural hyacinthacines B5 and B7 are the same compounds; however, without access to authentic samples this cannot be unequivocally proven.

UOW Authors


  •   Savaspun, Kongdech (external author)
  •   Au, Christopher W. G. (external author)
  •   Pyne, Stephen

Publication Date


  • 2014

Citation


  • Savaspun, K., Au, C. W. G. & Pyne, S. G. (2014). Total synthesis of hyacinthacines B3, B4, and B 5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common precursor. Journal of Organic Chemistry, 79 (10), 4569-4581.

Scopus Eid


  • 2-s2.0-84900871384

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2720&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1702

Has Global Citation Frequency


Number Of Pages


  • 12

Start Page


  • 4569

End Page


  • 4581

Volume


  • 79

Issue


  • 10

Place Of Publication


  • United States

Abstract


  • The total synthesis of hyacinthacines B3, B4, and B5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common anti-1,2-amino alcohol precursor is described. These syntheses confirmed that the proposed structures and absolute configurations of hyacinthacines B3, B4, and B5 were correct and disclosed that the proposed structure of hyacinthacine B7 was incorrect. Our synthetic and spectroscopic studies suggest that the natural hyacinthacines B5 and B7 are the same compounds; however, without access to authentic samples this cannot be unequivocally proven.

UOW Authors


  •   Savaspun, Kongdech (external author)
  •   Au, Christopher W. G. (external author)
  •   Pyne, Stephen

Publication Date


  • 2014

Citation


  • Savaspun, K., Au, C. W. G. & Pyne, S. G. (2014). Total synthesis of hyacinthacines B3, B4, and B 5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common precursor. Journal of Organic Chemistry, 79 (10), 4569-4581.

Scopus Eid


  • 2-s2.0-84900871384

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2720&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1702

Has Global Citation Frequency


Number Of Pages


  • 12

Start Page


  • 4569

End Page


  • 4581

Volume


  • 79

Issue


  • 10

Place Of Publication


  • United States