Abstract
A synthesis of alstoscholarinoid B (1) and 3β-acetoxy-11α-hydroxy-11(12 → 13)abeooleanan-12-al (2) has been accomplished in 7-9 steps and 10%-16% overall yield from oleanolic acid. This synthesis featured a bioinspired SmI2-mediated reductive aldol reaction to establish the abeo-11(12 → 13)-oleanane framework of both 1 and 2 and a retro-aldol/aldol/lactonization cascade to fully construct the skeleton of 1. Moreover, the investigation of the bioinspired aldol reaction also sheds light on the potential biogenesis of natural products.
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