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

Authors

Kongdech Savaspun, University of WollongongFollow
Christopher W. G Au, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

90556

Publication Details

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.

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.

Grant Number

ARC/DP130101968

Additional Grant Number

http://purl.org/au-research/grants/ARC/DP130101968