Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B.
The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1-C25 Diels-Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels-Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.
Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University Medical Center, Nashville, Tennessee 37232, USA.
Leslie N
LN
Aldrich
Eric S
ES
Dawson
Craig W
CW
Lindsley
D032701:Biomimetics; D004579:Electron Transport; D008958:Models, Molecular; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000378:metabolism*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000378:metabolism*; D013302:Streptomyces / Q000378:metabolism
D011758:Pyrroles; D013141:Spiro Compounds; C543079:marineosin A; C543080:marineosin B