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Syntheses of Batzelline A, Batzeline B, Isobatzelline A, and Isobatzelline B
Author(s) -
Alvarez Mercedes,
Bros M. Antonieta,
Gras Gemma,
Ajana Wadi,
Joule John A.
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(199905)1999:5<1173::aid-ejoc1173>3.0.co;2-o
Subject(s) - chemistry , total synthesis , substituent , stereochemistry , quinoline , electrophile , tricyclic , electrophilic substitution , medicinal chemistry , organic chemistry , catalysis
Batzellines A and B ( 1a , b ) and isobatzellines A and B ( 2a , b ) are 1,3,4,5‐tetrahydropyrrolo[4,3,2‐ de ]quinoline‐containing marine alkaloids characterized by the presence of a methylthio substituent at C‐2 of the tricyclic system. We describe here the total synthesis of these natural compounds following the synthetic strategy that we have used previously for the synthesis of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A, B, C, and D. The introduction of the methylthio group by electrophilic substitution of a pyrrolo[4,3,2‐ de ]quinoline, appropriately substituted and in a suitable oxidation state, is the key step in the success of these syntheses.