1427556-52-2

Upstream product

• 203315-97-3 (R)-2,2-dimethyl-3-(3-methylpent-4-en-1-yl)oxirane 
• 663176-48-5 (R,E)-ethyl 6-methylocta-2,7-dienoate 
• 1427556-49-7 (R)-methyl 6-methyloct-7-enoate 
• 10281-56-8 (R)-3,7-dimethyl-1,6-octadiene 
• 63215-85-0 (R)-4-methylhex-5-enal 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 109529-06-8 7-[(tert-butyldimethylsilyl)oxy]heptanal 
• 77744-45-7 7-((tert-butyldimethylsilyl)oxy)heptanoic acid 
• 1388220-76-5 (R)-6-methyloct-7-en-1-ol 
• 126696-08-0 7-(tert-butyldimethylsilyloxy)heptan-1-ol 

Downstream Products

• 1427556-65-7 (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate 
• 1427556-63-5 (4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate 
• 1427556-54-4 (S)-4-benzyl-3-[(2S,6R)-2,6-dimethyloct-7-enoyl]oxazolidin-2-one 

Relevant academic research and scientific papers

Synthetic studies of carolacton: Enantioselective total synthesis of C1-C8 and C9-C19 fragments of the molecule

This paper describes synthetic studies towards carolacton, a highly potent antibiotic against dental caries and endocarditis related bacterium Streptococcus mutans. The synthesis of the 12-membered lactone with a diversely functionalized keto acid side chain was accomplished by utilizing a blend of chiral pool and aldol strategies. Carbon chain C1-C8 was derived by utilizing Paterson aldol methodology and a Corey-Fuchs reaction. The C9-C19 chain was prepared by means of iterative Evans asymmetric alkylations and an E-selective cross-metathesis reaction. Georg Thieme Verlag Stuttgart New York.

Studies toward the total synthesis of carolacton

An efficient synthesis of the C1-C19 segment of carolacton is described, starting from d-ribose, (-)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki-Hiyama-Kishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions. Georg Thieme Verlag Stuttgart New York.