266675-80-3Relevant academic research and scientific papers
Studies toward norzoanthamine: Ireland–Claisen rearrangements of α,β-unsaturated esters in a stereocontrolled synthesis of trans-fused 2-cyclohexen-1-ones
Gladen, Paul T.,Patnaik, Samarjit,Williams, David R.
, (2021)
The enantiocontrolled preparation of the trans-fused ABC ring system of norzoanthamine is described. The synthesis strategy has incorporated studies of Ireland–Claisen rearrangements of esters derived from 3,3-dimethylacrylic acid. Stereocontrol results from competing chair- and boat-like transition states. Introduction of a nitroalkene by application of a modified Henry reaction facilitates an intramolecular Diels–Alder cycloaddition for an effective and simple transformation to the desired conjugated decalone. A fully functionalized AB ring system leads to the cyclization of the trans-fused cyclohexenone to complete the ABC system via ring-closing metathesis.
Intramolecular Diels-Alder cyclizations of (E)-1-nitro-1,7,9-decatrienes: Synthesis of the AB ring system of norzoanthamine
Williams, David R.,Brugel, Todd A.
, p. 1023 - 1026 (2007/10/03)
Cyclizations of substituted (E)-1-nitro-1,7,9-decatrienes under thermal and Lewis acid conditions have led to the formation of decalin ring systems with excellent endo selectivity. This strategy has been applied to the synthesis of the AB ring system of n
