862509-67-9

Upstream product

• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 392692-60-3 (2R,4S,5R)-9-chloro-5-hydroxy-2-(p-methoxybenzyloxy)-4-methyl-nonan-3-one 
• 392692-59-0 2-p-methoxybenzyloxy-3-pentanone 
• 14273-86-0 methyl 5-chloropentanoate 
• 20074-80-0 5-chloro-pentanal 

Downstream Products

• 392692-65-8 C₆₃H₉₆BClO₁₁Si 
• 392692-67-0 C₆₂H₉₄Cl₂O₁₂Si₂ 
• 392692-68-1 C₆₃H₉₆Cl₂O₁₁Si₂ 
• 392692-66-9 1-[6-[[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-7-chloro-4-hydroxy-octa-5,7-dien-2-one 
• 537041-15-9 (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran 
• 392692-64-7 1-[(2R,3R,4R,5R,6R)-6-[(S)-[(2R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one 
• 392692-63-6 (2R,4S,5R,6R)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran-4-ol 
• 392692-62-5 (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one 

Relevant academic research and scientific papers

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The southern hemisphere EF segment

The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran. The Royal Society of Chemistry 2005.

Stereocontrolled total synthesis of (+)-altohyrtin A/spongistatin 1

As an exceptionally potent antimitotic macrolide, altohyrtin A/spongistatin 1 shows great promise in cancer chemotherapy but its extreme scarcity in the natural sponges has halted its further preclinical development. A highly stereocontrolled total synthe