Chen, XiaochuanChen, JinchunZhu, Jieping2010-11-252010-11-252010-11-25200610.1055/s-2006-950343https://infoscience.epfl.ch/handle/20.500.14299/58454A concise synthesis of a highly functionalized, orthogonally protected amino triol I (R = CH2Ph, R1 = SiPh2CMe3) was achieved via a Mannich reaction between a corresponding phenol II and a chiral oxazinone III as a key step. The utility of such an approach is illustrated by a concise synthesis of a highly oxygenated tetrahydroisoquinoline IV (R = CH2Ph), a key structural unit of ecteinascidin 743 (Et 743) and related natural products. [on SciFinder (R)]Mannich reaction (asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); Alkaloids Role: SPN (Synthetic preparation)PREP (Preparation) (isoquinoline; asym. synthesis of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction); Stereoselective synthesis (of a highly oxygenated tetrahydroisoquinoline ecteinascidin 743 subunit via a key phenolic Mannich reaction)ecteinascidin 743 subunit asym synthesis phenolic Mannich reaction; tetrahydroisoquinoline ecteinascidin 743 subunit asym synthesis phenolic Mannich reaction; alkaloid ecteinascidin 743 subunit asym synthesis phenolic Mannich reactiontext::journal::journal article::research article