Concise Syntheses of Harmicine and a Pyrrolidinoisoquinoline Derivative Using Chiral 1-Allyl Adducts of β-Carboline and Isoquinoline as Starting Materials

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Total syntheses of (S)-harmicine and (R)-1,2,3,5,6,10bhexahydropyrrolo[2,1-a]isoquinoline were carried out using chiral 1-allyl-1,2,3,4tetrahydro-β-carboline and 1-allyl-1,2-dihydroisoquinoline as starting materials, respectively.In recent years, we have developed a new method by which allyl group was introduced at C-1 position of β-carboline or isoquinoline derivatives using chiral auxiliaries derived from readily available amino acids.Thus, 1-allyl-1,2-dihydro derivatives of isoquinolines 2 and β-carbolines 3 were obtained in a highly diastereoselective manner.Allyl group is a versatile tool for syntheses of other functional groups, 4 and there are several reports concerning the application of racemic allyl group of β-carboline to the synthesis of various alkaloids. 5In order to prove the usability of the chiral allyl adducts obtained