ja003292c_si_001.pdf (1.09 MB)
Stereochemical Elucidation and Total Synthesis of Dihydropacidamycin D, a Semisynthetic Pacidamycin
journal contribution
posted on 2001-01-11, 00:00 authored by Constantine G. Boojamra, Rémy C. Lemoine, Julie C. Lee, Roger Léger, Karin A. Stein, Nicole G. Vernier, Angela Magon, Olga Lomovskaya, Patrick K. Martin, Suzanne Chamberland, May D. Lee, Scott J. Hecker, Ving J. LeeHydrogenation of the C(4‘) exocyclic olefin of the pacidamycins has been shown to produce a
series of semisynthetic compounds, the dihydropacidamycins, with antimicrobial activity similar to that of the
natural products. Elucidation of stereochemistry in the pacidamycins has been completed through a campaign
of natural product degradation experiments in combination with the total synthesis of the lowest-molecular
weight dihydropacidamycin, dihydropacidamycin D. The stereochemical identities of the tryptophan and two
alanine residues contained in pacidamycin D have been shown to be of the natural (S) configuration, and the
unique 3-methylamino-2-aminobutyric acid contained in this series of antibiotics has been shown to be of the
(2S,3S) configuration. Finally, the stereochemistry obtained by hydrogenation of the C(4‘)−C(5‘) exocyclic
olefin has been shown to be (R) at the C(4‘) nucleoside site.