Natural product synthesis Carbon–hydrogen bond activation

1 natural product synthesis

1.1 (+)-lithospermic acid via c-h activation
1.2 calothrixin , b via c-h activation
1.3 mescaline analogue via c-h activation

natural product synthesis

the development of methodology c-h activation has impacted natural product synthesis, @ least in academic realm. ideally, synthetic routes contain minimal steps, while maximizing yield. c-h activation has enabled researchers activate c-h bonds in highly functionalized molecules.

the product in above reaction common scaffold multiple natural products, including hapalindole q , ambiguine h. core structure can made through c-c bond (blue bond in product) formation via c-h activation. innate reactivity of indole , enolate leads formation of c-c bond form indole-carvone intermediate.

(+)-lithospermic acid via c-h activation

the total synthesis of lithospermic acid employs guided c-h functionalization late stage highly functionalized system. directing group, chiral nonracemic imine, capable of performing intramolecular alkylation, allows rhodium-catalyzed conversion of imine dihydrobenzofuran.

calothrixin , b via c-h activation

the total synthesis of calothrixin , b features intramolecular pd-catalyzed cross coupling reaction via c-h activation, example of guided c-h activation. cross coupling occurs between aryl c-i , c-h bonds form c-c bond (highlighted in red).

mescaline analogue via c-h activation

the synthesis of mescaline analogue, has interesting biological properties, employs, specifically, rhodium-catalyzed enantioselective annulation of aryl imine via c-h activation.