Journal
TETRAHEDRON LETTERS
Volume 53, Issue 36, Pages 4892-4895Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.011
Keywords
Natural product; Benzonaphthyridine alkaloid; Total synthesis; Absolute configuration
Categories
Funding
- National Science Foundation of China [30901845]
- National Basic Research Program of China '973' [2012CB721001]
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The first total synthesis of benzonaphthyridine alkaloid (1), a unique diazaphenathrene alkaloid isolated from mangrove-derived Streptomyces albogriseolus, was accomplished. The core structure was unequivocally constructed via several key transformations, such as Knoevenagel condensation, Curtius rearrangement, and cyclic carbamate formation-reduction sequence. The chiral unsaturated ketone acid moiety was synthesized from N-tert-butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester (15). The absolute configuration was determined. (C) 2012 Elsevier Ltd. All rights reserved.
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