Home Alternatives in the Design of Chemical Synthesis
- Slides: 32
Home Alternatives in the Design of Chemical Synthesis • Combining process and medicinal chemistry • Designing for all desired targets • Avoiding unnecessary complication
Home Alternatives in the Design of Chemical Synthesis The Target Molecules Euthyroides episcopalis Cystodytes sp.
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets • Natural products are interconnected by virtue of their biosynthesis from ubiquitous starting materials
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets • In the case of new natural products the connectivity may be deduced based on our understanding of chemical reactivity
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets • In the case of new natural products the connectivity may be deduced based on our understanding of chemical reactivity
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Euthyroideones • Due to the unusual structural features of the euthyroideones they represent a trivial case of mapping
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Euthyroideones • Euthyroideones B and C appear to be oxidation products of euthyroideone A • However, since the overall structure shows a high • The hypothetical fully unsaturated euthyroideone oxidation state it may be assumed that B and C arise cannot be disregarded as a possible precursor by further oxidation of A
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Deconstructing the Skeleton
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Deconstructing the Skeleton
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Deconstructing the Skeleton
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Discovery It is important to remember that reagents may participate in multiple reaction types.
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Discovery Bromine is also an oxidant
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Discovery -H 2 O
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Discovery The point at which the CBz falls off is unclear This unusual transformation provides a product with many of the features of the desired target molecule
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Discovery vs. This is particularly striking since it provides a means of differentiating the two reactive aromatic positions
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Design ? ? ? Since the literature lacks a transformation capable of linking these two structures, we must move on to other approaches we must create one
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Design The obstacle that presents itself in the elaboration of this structure is the reversibility of the Pictet-Spengler reaction
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Reaction Design Replacing formaldehyde with glyoxilic acid provides a means of making the cyclization irreversible.
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Euthyroideones X The seemingly trivial methylation/oxidation necessary to complete this synthesis proved unworkable, and completion of the synthesis remains an elusive goal.
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Pyridoacridines Acridine Pyridoacridine • The Arnoamines are part of a larger class of natural products – the pyridoacridines
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Pyridoacridines Dopamine-derived pyridoacridine • The arnoamines are part of a larger class of natural products – the pyridoacridines
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Pyridoacridines Dopamine-derived pyridoacridines
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Arnoamines • The Arnoamines are related by methylation • The Arnoamines are part of a larger class of natural products – the pyridoacridines
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Arnoamines Styelsamine D • Arnoamine A may be related to the other pyridoacridines by side chain cyclization
Home Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets The Arnoamines Styelsamine D • Styelsamine D was designated the primary target since it appears to be central to all dopamine-derived pyridoacridines
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis Styelsamine B
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis Styelsamine B
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis Styelsamine B
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis Styelsamine B
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis The Pyridoacridine Family
Home Alternatives in the Design of Chemical Synthesis Mechanism for Synthesis The Pyridoacridine Family
Alternatives in the Design of Chemical Synthesis Planning for Multiple Targets Mechanism for Synthesis The Big Picture • Take into account all desired target molecules as a guide to synthetic design • Be willing to explore new reaction chemistry • One unknown step may be preferable to several known steps Home
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