Flexible approach for the asymmetric synthesis of (−)-hyacinthacine A1 and its 7a-epimer

The diastereoselective nucleophilic addition of organic boronic ester to 3-hydroxy-2-substituted N-acyliminium ions 9 led to the formation of 2,5-cis-pyrrolidine 10, from which a convenient synthesis of (−)-7a-epi-1 was developed. In addition, an efficient asymmetric synthesis of (−)-hyacinthacine A1 1 was achieved through the reduction/ring-opening process.

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