Synthesis of Protected 4‐Deoxyaklanonic Acid via Naphthalene‐substituted Oligoketides | Zendy

Krohn Karsten | Zendy; Schäfer Gisbert | Zendy

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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 ).

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