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A New Approach to Erythrinanes through Pummerer‐Type Cyclization
Author(s) -
Jousse Céline,
Desmaële Didier
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199904)1999:4<909::aid-ejoc909>3.0.co;2-7
Subject(s) - chemistry , sulfoxide , intramolecular force , pummerer rearrangement , michael reaction , aldehyde , nitro , aldol reaction , derivative (finance) , stereochemistry , aryl , bicyclic molecule , medicinal chemistry , intramolecular reaction , organic chemistry , catalysis , acetic anhydride , alkyl , financial economics , economics
A successful new strategy for the synthesis of erythrinanes is reported. (Nitromethyl)arene derivative 16 was condensed with aldehyde 17 to give nitro aldol 19 . After removal of the hydroxy group, the subunits 26a , b , containing the erythrinane rings A and D, were formed by intramolecular Michael addition. Reduction of the nitro function, followed by cyclization of the resulting amino group with the appended acetate group afforded the bicyclic lactams 29a , b , bearing an angular aryl group. Two‐carbon elongation at the nitrogen atoms of 29a and 29b by means of hetero Michael addition of methyl phenyl sulfoxide, followed by Pummerer‐type cyclization, gave cis ‐ and trans ‐11‐phenylthioerythrinan‐8‐ones 35a and 35b , respectively. Reductive desulfurization at C‐11 furnished the desired erythrinan‐8‐ones 39a and 39b in 8 steps from 16 .