Kainoid amino acids are a unique group of non‐proteinogenic pyrrolidinedicarboxylic acids. The parent member, (–)‐α‐kainic acid (originally known as digenic acid), has attracted considerable interest, largely because of its neuroexcitatory properties, as well as its pronounced insecticidal and anthelmitic activities. Because these activities are strongly due to its stereochemistry, (–)‐α‐kainic acid represents a considerable synthetic challenge, and many groups have therefore reported syntheses of kainic acids, as well as of kainoid analogues. This article is intended to review the total synthesis of kainic acid from 1996 until the end of 2011.

Conventional synthetic transformations such as Wittig olefination, catalytic hydrogenation and lactonization reactions were used to obtain enantiomerically pure (R)-γ-caprolactone and (S)-japonilure, pheromones of the beetle Trogoderma and the Osaka beetle Anomala osakana, respectively, as well as the hydroxylated γ-lactone L-factor from 2,3-O-isopropylidene-D-or Lerythrose.

A new synthesis of (Ϯ)-1-deoxy-6-epi-castanospermine and (Ϯ)-1-deoxy-6,8a-di-epi-castanospermine has been developed, starting from the hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate and ethyl vinyl ether. Appropriate terminal dienes were prepared by standard manipulations, which,

The synthesis of (±)-crispine A in 9 steps and 24% overall yield was achieved using a nitrosoalkene hetero-Diels-Alder addition to ethyl vinyl ether as the key step. The synthesis starts from commercial 3,4-dimethoxyphenylacetic acid and uses simple methods, easily accessible materials and inexpensive reagents. An isochroman derivative was unexpectedly formed in an attempted reduction of a dihydro-4H-1,2-oxazine intermediate.

Review: 92 refs.