196860-46-5

Upstream product

• 53346-05-7 (R)-2-benzyloxypropanal 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 

Downstream Products

• 196860-47-6 (2R,3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentan-1-ol 
• 196860-48-7 [(1S,2S)-1-((R)-1-Benzyloxy-ethyl)-3-iodo-2-methyl-propoxy]-tert-butyl-dimethyl-silane 
• 196860-50-1 (2S,3S,4R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal 
• 196860-56-7 (4R,4aS,5S,6R,7R,8R,8aR)-5,7-Bis-benzyloxy-4-[(E)-(3R,4S,5R)-5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-hex-1-enyl]-8-methoxymethoxy-6-methyl-octahydro-naphthalen-2-one 
• 196860-53-4 (4R,5S,6R)-6-Benzyloxy-2-[(1S,3R,4S,5S,6R,7R,8R,9R)-5,7-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-6-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl]-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-en-3-ol 

Relevant academic research and scientific papers

Approach towards an EPC-synthesis of nodusmicin - IV. Construction of the highly hindered trisubstituted double bond of nodusmicin - IV. Construction of the highly hindered trisubstituted double bond of nodusmicin

The highly substituted subunit 6 of our convergent synthesis of nodusmicin was prepared utilizing Evans' oxazolidinone protocol. Compound 6 was then adjoined to the decalin subunit 7 using Martin's olefination method. To improve on the formation of the hindered trisubstituted double bond, the following model reactions were devised: reductive coupling of ester and keto functionality of tricycle 16 led to the α-hydroxyketone, which was converted to the cyclic sulfate 19 via the diol. Sodium naphthalide then converted 19 to the olefins 20.