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Synthesis of Protected 4‐Deoxyaklanonic Acid via Naphthalene‐substituted Oligoketides
Author(s) -
Krohn Karsten,
Schäfer Gisbert
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960217
Subject(s) - chemistry , naphthalene , naphthoquinone , side chain , base (topology) , cascade , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , chromatography , mathematical analysis , mathematics , polymer
Ketide side chains (C 4 ) were attached to the naphthoquinone 3 by reaction with the dienes 4 or 14 followed by Baker‐Venkataraman rearrangement of esters 8 and 17 to attach the second protected β‐diketo side chain. Linear anellations of the corresponding naphthoquinone precursors 9 and 17 to the 4‐deoxyaklanonic acids 10 and 18a , respectively, were effected in a base‐catalyzed cascade of reactions (e.g. only three operations from 3 to 18a ).