128243-83-4

Upstream product

• 116428-25-2 (E)-(6S,7R)-14-Benzyloxy-6-methoxymethoxy-2,6,10-trimethyl-9-phenylsulfanyl-tetradeca-2,10-dien-7-ol 
• 116216-79-6 4-Benzyloxy-1-[(R)-5-((S)-1-methoxymethoxy-1,5-dimethyl-hex-4-enyl)-2-methyl-tetrahydro-furan-2-yl]-butan-1-ol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 116216-80-9 (2R,3S,6R)-2-<3-(Benzyloxy)propyl>tetrahydro-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-3-methyl-2H-pyran-3-ol 
• 119840-63-0 (E)-(2S,9R)-9-Benzyloxy-2-[(2R,4aR,6R,8aS)-6-((S)-1-methoxymethoxy-1,5-dimethyl-hex-4-enyl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-6,10-dimethyl-4-phenylsulfanyl-10-(2-trimethylsilanyl-ethoxymethoxy)-undec-5-en-2-ol 
• 119840-67-4 (2-{(E)-(2R,9S)-2-Benzyloxy-9-methoxymethoxy-9-[(2R,4aR,6R,8aS)-6-((S)-1-methoxymethoxy-1,5-dimethyl-hex-4-enyl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1,1,5-trimethyl-7-phenylsulfanyl-dec-5-enyloxymethoxy}-ethyl)-trimethyl-silane 

Relevant academic research and scientific papers

Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol

The first total syntheses of (+)-thyrsiferol (1), (+)-thyrsiferyl 23-acetate (3), and (+)-venustatriol (5) have been accomplished in a stereoselective manner.An effective synthetic scheme to construct the BC ring system, which adopts a chair/twist-boat conformation, was first developed by means of a model study.This method involves stereoselective formation of the strained C ring by intramolecular attack of the C7-hydroxyl group at the C3-postion of the 2,3-epoxy alcohol, employing titanium tetraisopropoxide as an acidic activator.Based on the information accumulated in the model study and retrosynthetic considerations, the total syntheses of 1,3, and 5 were performed in the sequence of (1) construction of the BC ring system equipped with a C1-C6 carbon unit, (2) elongation of the C17-C24 carbon chain, (3) formation of a D ring through the stereoselective epoxidation of the 4-en-1-ol system and successive cyclization, and (4) construction of the A ring by bromonium ion induced cyclization of the 4-en-1-ol system.