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Total Synthesis of the Proposed Structure of the Anthrapyran Metabolite δ‐Indomycinone
Author(s) -
Tietze Lutz F.,
Singidi Ramakrishna Reddy,
Gericke Kersten M.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700823
Subject(s) - metabolite , chemistry , stereochemistry , computer science , biochemistry
Abstract The first total synthesis of the proposed structure of δ‐indomycinone has been accomplished. The key steps involve the Diels–Alder reaction of a bromonaphthoquinone ( 6 ) and 1‐methoxy‐3‐methyl‐1‐trimethylsiloxy‐1,3‐butadiene ( 7 ) to access the anthraquinone skeleton, representing a common building block of other naturally occurring anthraquinone antibiotics, regioselective bromination of anthraquinone ( 14 ) and a highly diastereoselective alkylation of enantiomerically pure dioxolanone 8 . The reported synthetic approach has the advantage of high yields, excellent selectivity and a remarkable general applicability for the total synthesis of other anthrapyran natural products. The spectroscopic data obtained for the synthetic compounds 2 and 36 are not in agreement with those reported for the natural product, and therefore revision of the assigned structure is required.