199857-44-8

Upstream product

• 128461-65-4 3-(p-methoxybenzyloxy)propanal 
• 199857-43-7 C₃₄H₆₃BO₂Si 
• 199857-42-6 (S)-3-methyl-4-(triisopropylsiloxy)-butan-2-one 
• 158783-85-8 (S)-N-methoxy-N-methyl-3-triisopropylsilanyloxy-2-methylpropionamide 
• 158783-84-7 (S)-methyl 2-methyl-3-(triisopropylsilyloxy)propanoate 
• 13154-24-0 triisopropylsilyl chloride 
• 199857-59-5 C₃₄H₆₃BO₂Si 

Downstream Products

• 199857-51-7 Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester 
• 199857-52-8 Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-8-((R)-4-hydroxy-3-methyl-2-methylene-butyl)-10-methyl-1,7-dioxa-spiro[5.5]undec-4-yl ester 
• 199857-56-2 (4S,5S,6R,9S)-5-Hydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-methylene-undecan-3-one 
• 199857-53-9 (2R,5S)-5-Methoxy-7-(4-methoxy-benzyloxy)-2-methyl-3-methylene-heptanal 
• 862379-32-6 (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(triethylsiloxy)-hex-1-ene 
• 199857-46-0 (4R)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(triethylsiloxy)-hex-1-ene 
• 199857-47-1 (3S)-1-(p-methoxybenzyloxy)-5-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-hex-5-en-3-ol 
• 199857-48-2 (3S,5S,9S,11S)-1-benzyloxy-5-(t-butyldimethylsiloxy)-9-hydroxy-13-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-3,11-bis(triethylsiloxy)-tetradec-13-en-7-one 
• 862379-33-7 (2S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undecan-4-one 
• 199857-50-6 (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-4-methyl-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol 
• 862379-31-5 (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene 
• 199857-49-3 (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol 
• 862379-36-0 (2S,5S)-7-(4-Methoxy-benzyloxy)-2-methyl-5-triethylsilanyloxy-1-triisopropylsilanyloxy-heptan-3-one 

Relevant academic research and scientific papers

Studies in marine macrolide synthesis: Synthesis of the C1-C15 subunit of spongistatin 1 (altohyrtin A) and 15,16-anti aldol coupling reactions

The C1-C15 aldehyde 3, containing the AB-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from methyl ketone (S)-8. The C15 and C16 stereocentres could be introduced together, relying on Felkin-Anh control, by using a boron-mediated, anti aldol coupling reaction, as in 22 → 25 and 26.

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The AB-spiroacetal segment

The convergent synthesis of the C1-C15 AB-spiroacetal subunit 2 of altohyrtin A/spongistatin 1 (1) is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc2BCl mediation, t