219498-13-2

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 219498-24-5 (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol 
• 103791-04-4 Benzyloxymethyl isopropenyl ketone 
• 219498-12-1 [(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy]-tert-butyl-dimethyl-silane 
• 219498-10-9 (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone 
• 219566-61-7 (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one 
• 219498-11-0 (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 71312-19-1 (+/-)-1-benzyloxy-3-methyl-but-3-en-2-ol 

Relevant academic research and scientific papers

A direct and efficient stereocontrolled synthetic route to the pseudopterosins, potent marine antiinflammatory agents

Described herein is a new synthetic route to pseudopterosin aglycone (3), a key intermediate for the synthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and E (2). The pathway of synthesis starts with the abundant and inexpensive (S)-(-)-limonene and its long-known cyclic hydroboration product (4) and leads to the chiral hydroxy ketone 6. Conversion of 6 to 10 followed by a novel aromatic annulation produced 15 which underwent a highly diastereoselective cyclization to afford the protected pseudopterosin aglycone 16. The naturally occurring pseudopterosins such as 1 and 2 are readily available from this key intermediate.