Methyl palustrate

High-pressure organic chemistry. Part 17. Diels-Alder reaction of methyl palustrate with maleic anhydride and N-phenylmaleimide [87]... 

Figure 7.1 Total ion current (TIC) chromatogram obtained by GC-MS analysis of a resin (Pinus sylvestris). The diterpenoid resin acids were methylated (using diazomethane) to improve chromatographic performance. Peak identities 1, Methyl pimarate 2, Methyl sandaracopimarate 3, Methyl isopimarate 4, Methyl palustrate 5, Methyl dehydroabietate 6, Methyl abietate 7, Methyl neoabietate. For GC-MS operating conditions, see Heron and Pollard (1988).

Kotsuki H., Kataoka M., Matsuo K., Suetomo S., Shiro M., Nishizawa H., High-pressure organic-chemistry. 17. Diels-Alder reaction of methyl palustrate with maleic-anhydride and JV-phenyhnaleimide, J. Chem. Soc. Perkin Trans. 1,22,1993,... 

The multicomponent reaction for the synthesis of disubstituted piperidines developed by Tailor and Hall involves a normal electron demand Diels-Alder reaction in tandem with an allyboration. This strategy has allowed for the synthesis of (-)-methyl dihydropalustramate 148 (Scheme 41.31), a degradation product of the toxic alkaloid palustrine of marsh horse tail Equisetum palustre The reaction of 4-borono-l-hydrazonodiene 142, Waldner... 

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