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The synthesis of the cationic lipid SST-01, a key component of Kyowa Kirin's siRNA−lipid nanoparticles, through a two-step homogeneous continuous-flow process is described. Safe and scalable aerobic oxidation with a catalytic Cu I /TEMPO system and diluted oxygen (5% O 2 in N 2 ) was utilized in the first step to provide a lipid aldehyde. Subsequent reductive amination of the first-step eluent with methylamine using tetramethylammonium triacetoxyborohydride provided the target SST-01 in an overall yield of 95%.

Rev. -A synthetic pathway to 5,6-dihydrovaltrate (I) is described using an asymmetric Diels-Alder reaction between diethyl fumarate and cyclopentadiene as key step (catalyst and product configuration are not specified, yield quant., 95% e.e.). Because of similar biological potency to valtrate, the bioisostere (I) can be recognized as a promising scaffold for new anti-HIV agents. -(TAMURA, S.; SHIMIZU, N.; FUJIWARA, K.; KANEKO, M.; KIMURA, T.; MURAKAMI*, N.; Bioorg. Med.