314273-49-9

Upstream product

• 314273-46-6 (4R,5S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-yne 
• 219606-81-2 (3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene 
• 188926-24-1 (2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 314273-48-8 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthetic studies on the salicylihalamides: Macrolactone formation via ring closing metathesis versus macrolactonization

Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd.