184299-64-7

Upstream product

• 147384-55-2 calbistrin A 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 187038-26-2 (2E,4E,6E,8E)-(10R,11S)-10-(tert-Butyl-dimethyl-silanyloxy)-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 1-methyl ester 12-(2-trimethylsilanyl-ethyl) ester 
• 187038-24-0 (E)-(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-oxo-hex-4-enoic acid 2-trimethylsilanyl-ethyl ester 
• 187038-23-9 (E)-(2S,3R)-6-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl ester 
• 187038-22-8 (E)-(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl ester 
• 187038-27-3 (2E,4E,6E,8E)-(10R,11S)-10-(tert-Butyl-dimethyl-silanyloxy)-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 1-methyl ester 
• 187038-16-0 (3R,4aR,8S,10S,10aS,10bR)-10-Hydroxy-3-methoxy-4a,8,10b-trimethyl-2,3,4a,8,9,10,10a,10b-octahydro-benzo[f]chromen-1-one 
• 107184-58-7 (+/-)-methyl 3-acetoxy-2,4-dimethyl-hex-(4E)-enoate 
• 187038-21-7 (-)-(2S,3R)-methyl 3-acetoxy-2,4-dimethyl-hex-(4E)-enoate 
• 1197011-35-0 (E)-(2S,3R)-3-Hydroxy-2,4-dimethyl-hex-4-enoic acid methyl ester 

Relevant academic research and scientific papers

The first total synthesis of calbistrin A, a microbial product possessing multiple bioactivities

The octahydronaphthopyranone moiety is synthesized from methyl α-D-mannopyranoside through the intramolecular Diels-Alder reaction, and the tetraenedicarboxylic acid moiety is from the enzymatically prepared anti-compound. Both moieties were coupled to accomplish the total synthesis of calbistrin A and to disclose its absolute structure.