Synthetic studies towards (-)-lemonomycin, synthesis of fused tetracycles

The asym. synthesis of 1,3-lactol-bridged tetrahydroisoquinolines I [R = SiMe2CMe3, CH2Ph; R1 = CH2CH(CO2Me)2; R2 = CO2CH2Ph] was developed. Subsequent cyclizations of I (R = SiMe2CMe3, CH2Ph) under acidic conditions lead to the formation of a tricyclic enamides II [R = SiMe2CMe3, CH2Ph; R1 = CH2CH(CO2Me)2; R2 = CO2CH2Ph]. II [R = CH2Ph, R1 = CH2CH(CO2Me)2, R2 = CO2CH2Ph] was in turn converted to a tetracyclic compd. III. [on SciFinder (R)]


Published in:
Synlett, 11, 1691-1694
Year:
2006
Keywords:
Note:
CAN 145:438438
26-6
Biomolecules and Their Synthetic Analogs
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0936-5214
written in English.
200132-54-3 Role: CAT (Catalyst use), USES (Uses) (asym. synthesis of the 1,3-lactol-bridged tetrahydroisoquinoline subunit of (-)-lemonomycin); 276248-62-5P ((-)-Lemonomycin) Role: PNU (Preparation, unclassified), PREP (Preparation) (asym. synthesis of the 1,3-lactol-bridged tetrahydroisoquinoline subunit of (-)-lemonomycin); 100-39-0 (Benzyl bromide); 30934-97-5; 81477-94-3; 225938-52-3; 852536-16-4 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of the 1,3-lactol-bridged tetrahydroisoquinoline subunit of (-)-lemonomycin); 912654-98-9P; 912654-99-0P; 912655-00-6P; 912655-01-7P; 912655-02-8P; 912655-03-9P; 912655-04-0P; 912655-05-1P; 912655-11-9P; 912655-12-0P; 912655-13-1P; 912655-14-2P; 912655-15-3P; 912655-16-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of the 1,3-lactol-bridged tetrahydroisoquinoline subunit of (-)-lemonomycin); 912655-06-2P; 912655-07-3P; 912655-08-4P; 912655-09-5P; 912655-10-8P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of the 1,3-lactol-bridged tetrahydroisoquinoline subunit of (-)-lemonomycin)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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