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- W2134779415 abstract "Abstract An improved method for obtaining optically pure ( S )‐(l‐ p ‐menthen‐8‐yl)amine ( 12 ) has led to expedient syntheses of two hypothetical biogenetic intermediates on the way to aistoteline ( 7 ), namely ( S )‐( N )‐(l‐ p ‐menthen‐8‐yl)‐2‐(3‐indolyl)ethylamine ( 3 ) and ( S )‐( N )‐(l‐ p ‐menthen‐8‐yl)‐2‐(3‐indolyl)ethylideneamine ( 4 ). The latter has been transformed into (−)‐hobartine ( 6 ) in 64% yield via a stereoselective biomimetic cyclization by treatment with HCOOH. This unambiguous synthesis establishes the hitherto unknown absolute configuration of (−)‐hobartin ( 6 ). Several model cyclization reactions of N ‐substituted α‐(terpen‐8‐yl)imine derivatives yielding unsaturated 3azabicyclo [3.3.1]nonane compounds are described." @default.
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- W2134779415 date "1984-06-20" @default.
- W2134779415 modified "2023-09-29" @default.
- W2134779415 title "Synthesis of (?)-Hobartine and Related Indole Alkaloids" @default.
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- W2134779415 doi "https://doi.org/10.1002/hlca.19840670417" @default.
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