The synthesis and antimicrobial activity of heterocyclic derivatives of totarol
The synthesis and antimicrobial activity of heterocyclic analogues of the diterpenoid totarol are described. An advanced synthetic intermediate with a ketone on the A-ring is used to attach fused heterocycles, and a carbon-to-nitrogen atom replacement is made on the B-ring by de novo synthesis. A-ring analogues with an indole attached exhibit, for the first time, enhanced antimicrobial activity relative to the parent natural product. Preliminary experiments demonstrate that the indole analogues do not target the bacterial cell division protein FtsZ as had been hypothesized for totarol.
Kim, Michelle B.,O'Brien, Terrence E.,Moore, Jared T.,Anderson, David E.,Ames, James B.,Shaw, Jared T.,Foss, Marie H.,Weibel, Douglas B.
supporting information
p. 818 - 822,5
(2012/12/12)
The synthesis and antimicrobial activity of heterocyclic derivatives of totarol
The synthesis and antimicrobial activity of heterocyclic analogues of the diterpenoid totarol are described. An advanced synthetic intermediate with a ketone on the A-ring is used to attach fused heterocycles, and a carbon-to-nitrogen atom replacement is made on the B-ring by de novo synthesis. A-ring analogues with an indole attached exhibit, for the first time, enhanced antimicrobial activity relative to the parent natural product. Preliminary experiments demonstrate that the indole analogues do not target the bacterial cell division protein FtsZ as had been hypothesized for totarol.
Kim, Michelle B.,O'Brien, Terrence E.,Moore, Jared T.,Anderson, David E.,Foss, Marie H.,Weibel, Douglas B.,Ames, James B.,Shaw, Jared T.
supporting information
p. 818 - 822
(2013/01/15)
Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes
(Equation Presented). An efficient, convergent synthesis of totarol by a diastereoselective epoxide/alkene/arene bicyclization is described. The reported synthesis enables the preparation of related diterpenes totaradiol and totarolone as well as previously unavailable derivatives that exhibit comparable inhibition of the bacterial cell division protein FtsZ.
Kim, Michelle B.,Shaw, Jared T.
supporting information; experimental part
p. 3324 - 3327
(2010/11/02)
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