405519-77-9

Upstream product

• 321527-28-0 N-[2-(4-bromo-1H-indol-3-yl)-ethyl]-2-(tert-butyl-diphenyl-silanyloxy)-acetamide 
• 303068-04-4 4-bromo-3-[(E)-2-nitro-1-ethenyl]-1H-indole 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 108061-74-1 2-(4-bromo-1H-indol-3-yl)ethan-1-amine 
• 603-83-8 3-nitro-o-tolylamine 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 52488-36-5 4-bromo-1H-indole 
• 321527-29-1 N-[2-(4-bromo-1H-indol-3-yl)-2-oxo-ethyl]-2-(tert-butyl-diphenyl-silanyloxy)-acetamide 

Downstream Products

• 321527-30-4 4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-1-methyl-1H-indole 
• 405519-78-0 4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indole 
• 761433-60-7 1-benzyl-4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-1H-indole 
• 761433-80-1 (S)-4-[3-((S)-7-{3-[2-(Dimethoxy-phosphorylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-3-formyl-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 761434-04-2 [5-(4-{(R)-3-[5-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-2-methoxy-phenyl]-3-hydroxymethyl-2,3-dihydro-benzofuran-7-yl}-1-methoxymethyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester 
• 761434-05-3 (S)-4-[3-((R)-7-{3-[2-(Dimethoxy-phosphorylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-3-hydroxymethyl-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 761433-79-8 4-[3-(3-(tert-butyl-dimethyl-silanyloxymethyl)-7-{3-[2-(dimethoxy-phosphorylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 321529-22-0 [5-(4-{3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-1-phenyl-ethyl]-2-methoxy-phenyl}-1-methyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

Studies toward diazonamide A: Initial synthetic forays directed toward the originally proposed structure

A brief introduction into the chemistry of diazonamide A (1) is followed by first-generation sequences to access the originally proposed structure for this unusual marine natural product. These explorations identified a route capable of delivering a model compound possessing the complete heteroaromatic core of the natural product, highlighting in the process several unanticipated synthetic challenges which led both to new methodology as well as an improved synthetic plan that was successfully applied to fully functionalized intermediates.

Chemistry and biology of diazonamide A: Second total synthesis and biological investigations

As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl 3.