For the purpose of organic syntheses of some corynanthe-type indole alkaloids, sesquiterpenes, and steroids, optically active intermediates cyclopentanone 3-allylalcohol, α-methylene-γ-butylo lactones andtrans-hydrindanone-propionic acid, were synthesized from (R)- and (S)-isopropylideneglyceraldehyde derived fromD-mannitol andLascorbic acid, respectively, utilizing Claisen rearrangement as a key reaction. Actually total syntheses of natural alkaloids, (-)-antirhine, (+)-dihydroantirhine and (-) dihydrocorynantheol were accomplished.
Volume 134, 2022
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