174874-04-5

Upstream product

• 174874-00-1 (5S,6S)-8-t-butyldimethylsilyloxy-6-chloro-1-tetrahydropyranyloxy-2-octyn-5-ol 
• 174874-02-3 (5S,6R)-8-t-butyldimethylsilyloxy-5,6-epoxy-2-octyn-1-ol 
• 174874-01-2 (5S,6S)-8-(tert-Butyl-dimethyl-silanyloxy)-6-chloro-oct-2-yne-1,5-diol 
• 137369-78-9 (2S,3S)-4-t-butyldimethylsilyloxy-3-chloropentane-1,2-diol 1-tosylate 
• 147618-57-3 Toluene-4-sulfonic acid (2S,3R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxiranylmethyl ester 
• 111466-32-1 (2S,3R)-4-t-butyldimethylsilyloxy-2,3-epoxy-pentan-1-ol 
• 98-88-4 benzoyl chloride 
• 174874-03-4 (5S,6R)-(2E)-8-t-butyldimethylsilyloxy-5,6-epoxy-2-octen-1-ol 

Downstream Products

• 174956-34-4 (5R,6R)-(2E)-1-benzoyloxy-5-bromo-2-octene-6,8-diol 
• 174874-05-6 (5R,6R)-(2E)-1-benzoyloxy-5-bromo-2-octene-6,8-diol 8-pivaloate 
• 174874-06-7 (5R,6R)-(2E)-1-benzoyloxy-5-bromo-6-t-butyldimethylsilyloxy-2-octene-8-ol 8-pivaloate 
• 174874-09-0 (2R,3R,5R,6R)-5-bromo-6-t-butyldimethylsilyloxy-2,3-epoxy-1-p-toluenesulfonyloxyoctan-8-ol 8-pivaloate 
• 174956-33-3 (5S,6R)-(2E)-1-benzoyloxy-5,6-epoxy-2-octen-8-ol 

Relevant academic research and scientific papers

Total synthesis of (-)-dactylynes

The first total synthesis of (-)-dactylyne (1) and (-)-isodactylyne (2), which have been isolated from sea hare, is described in detail. Critical steps in the synthesis include a stereoselective construction as well as an intramolecular ring closure of 32, and the effective double elongation reactions (59 → 63 and 64, 67 → 68, and 70 → 71).