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Versuche zur Synthese von Strychnopivotin und eine einfache Synthese des Isochinuclidin‐Gerüsts
Author(s) -
Teuber HansJoachim,
Tsaklakidis Christos,
Bats Jan Willem
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920182
Subject(s) - chemistry , nonane , derivative (finance) , diketone , stereochemistry , ring (chemistry) , octane , enamine , aldol reaction , organic chemistry , catalysis , financial economics , economics
Experiments Directed to the Synthesis of Strychnopivotine and a New Synthesis of the Isoquinuclidine Framework The 2‐azabicyclo[3.3.1]nonane (keto‐morphane) 2 can be transformed via the enamine 4 into the dithio‐dioxolane derivative 6 of the corresponding 6,7‐diketone. After hydrolysis of the dithio group and formation of the monoprotected diketone 3 Fischer cyclisation yields the isodasycarpidone derivative 7 , an intermediate to a synthesis of strychnopivotine ( 1a ). — In view of the likewise desired tricyclus 8 for a synthesis of strychnopivotine, a cyclisation of ketoamide 9 was tried under standard conditions. By aldol‐ring closure, however, not the expected 2‐azabicyclo[3.3.1]nonane 14 was formed, but instead the 2‐azabicyclo[2.2.2]octane derivative (isoquinuclidine) 15 . The preparation of 9 via the intermediates 10 – 13 is described.