Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam
التفاصيل البيبلوغرافية
العنوان:
Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam
The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultament-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 → 7) followed by saponification of the sultam moiety (7 → 4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61–71% overall yield. The Prelog-Djerassi lactonic acid 4 was synthesised in three steps (61–71% overall yield) starting from meso dialdehyde 5 utilizing a group-selective aldolization as a key step.
