Total Synthesis of Nominal Diazonamides—Part 1: Convergent Preparation of the Structure Proposed for (−)-Diazonamide A

@article{Li2001TotalSO,
  title={Total Synthesis of Nominal Diazonamides—Part 1: Convergent Preparation of the Structure Proposed for (−)-Diazonamide A},
  author={Jing Li and Susan Jeong and Lothar Esser and Patrick G. Harran},
  journal={Angewandte Chemie},
  year={2001},
  volume={40},
  pages={4765-4769}
}
Representative procedure for the preparation of 7: A solution of lithium hexamethyldisilazide in THF (1, 0.20 mL, 0.20 mmol) was added dropwise to a solution of 1 (0.038 g; 0.20 mmol) in THF (0.5 mL) at 78C. The resulting pale yellow solution was stirred for 10 min at the same temperature, and then a solution of coumarin 2b (0.032 g; 0.22 mmol) in THF (0.5 mL) was added dropwise at 78C. After 30 min, a solution of trans chalcone 5c (0.045 g, 0.22 mmol) was added dropwise. The reaction mixture… 
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In the preceding communication we described a fully synthetic pathway to the structure proposed for ( )-diazonamide A (1, Scheme 1).[1] This material is not identical to the natural product, which
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Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole
Model studies towards the synthesis of the cytotoxic marine natural product diazonamide A are described. Three model 3-phenylbenzo[b]furan derivatives 5, 8 and 10 were prepared using rhodium(II)
Progress toward synthesis of diazonamide A. Preparation of a 3-(oxazol-5-yl)-4-trifluoromethyl-sulfonyloxyindole and its use in biaryl coupling reactions.
TLDR
The synthesis of a 3-oxazol-5-yl-indole-4-triflate is described, featuring a Schölkopf reaction to prepare the oxazole and the participation of this intermediate in biaryl coupling reactions toward the total synthesis of the natural product diazonamide A is presented.
Total Synthesis of Nominal Diazonamides—Part 2: On the True Structure and Origin of Natural Isolates
In the preceding communication we described a fully synthetic pathway to the structure proposed for ( )-diazonamide A (1, Scheme 1).[1] This material is not identical to the natural product, which
Macrocyclic Triarylethylenes via Heck Endocyclization: A System Relevant to Diazonamide Synthesis
Received September 3, 1998 Diazonamide A (1, Figure 1) and its congeners1 are impressive products of invertebrate secondary metabolism wherein at least three proteinogenic amino acids have been
Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: approaches to diazonamide A.
TLDR
Two complementary strategies for the synthesis of the diazonamide A bisaryl quaternary center are described, which rely upon an extremely facile tandem cyclopropanation/ring-opening sequence and a more concise alkylation route ideal for material advancement.
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