537041-15-9

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 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 
• 20074-80-0 5-chloro-pentanal 
• 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 
• 392692-58-9 C₄₉H₆₇BO₈ 
• 392692-56-7 (3E,5R,6R,7R)-5,6-bis-(p-methoxybenzyloxy)-7-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-oct-3-en-2-one 
• 392692-55-6 methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate 
• 862509-67-9 (2R,4S,5R)-9-chloro-5-triethylsiloxy-2-(p-methoxybenzyloxy)-4-methyl-nonan-3-one 
• 392692-60-3 (2R,4S,5R)-9-chloro-5-hydroxy-2-(p-methoxybenzyloxy)-4-methyl-nonan-3-one 
• 862509-74-8 methyl (2S,3R,4R)-2,3-dihydroxy-4-[5-(R)-hydroxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate 
• 392692-61-4 (2S,3R)-7-chloro-2-methyl-3-(triethylsiloxy)-heptanal 
• 194934-59-3 methyl (2S,3R,4R)-4-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-2,3-dihydroxy-pentanoate 
• 194934-55-9 (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone 
• 194934-52-6 methyl (2E,4R)-4-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pent-2-enoate 

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 
• 862509-86-2 3-[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]-2-methyl-propane-1,2-diol 
• 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 

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.

Synthesis and biological evaluation of spongistatin/altohyrtin analogues: E-ring dehydration and C46 side-chain truncation

Simplified analogues of the potent antimitotic marine macrolide spongistatin 1/altohyrtin A were synthesised and evaluated as growth inhibitory agents against a range of human tumour cell lines, including Taxol-resistant strains, revealing that E-ring deh

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