201355-18-2

Upstream product

• 121289-23-4 p-methoxybenzyloxyacetaldehyde 
• 127793-65-1 (3S)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol 
• 201355-04-6 (2R,4S,6R,8R,10S)-8-Allyl-10-methoxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 862475-37-4 (2RS,4R)-5-(p-methoxybenzyloxy)-4-(triethylsiloxy)-pentane-1,2-diol 
• 201355-02-4 (R)-4-(p-methoxybenzyloxy)-3-(triethylsiloxy)-butanal 
• 201355-06-8 (4R,6R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-oct-1-en-4-ol 
• 201355-05-7 (3R)-3-methoxy-5-(tert-butyldimethylsilyloxy)-pentanal 
• 862475-32-9 (3S)-1-(tert-butyldimethylsilyloxy)-3-methoxy-hex-5-ene 
• 194342-84-2 (R)-1-[(4-methoxybenzyl)oxy]pent-4-en-2-ol 
• 201355-00-2 (2R,4S,8S,10R)-10-(t-butyldimethylsiloxy)-4-hydroxy-8-methoxy-1-(p-methoxybenzyloxy)-2-(triethylsiloxy)-12-tridecen-6-one 
• 201355-07-9 C₃₆H₆₅BO₃Si 
• 201355-01-3 (4S,6R)-6-(t-butyldimethylsiloxy)-4-methoxy-8-nonen-2-one 
• 862475-08-9 (4R,6R,8R)-8-benzyloxy-4-(t-butyldimethylsiloxy)-6-methoxy-1-nonene 
• 862475-29-4 (2R,4R,6R)-6-(t-butyldimethylsiloxy)-4-methoxy-8-nonen-2-ol 

Downstream Products

• 862475-31-8 (2R,4S,6R,8R,10S)-[10-(t-butyldimethylsiloxy)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecan-2-yl]-ethanal 
• 201354-99-6 1-[(2S,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undec-2-yl]butan-2-one 

Relevant academic research and scientific papers

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

Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.

Studies in marine macrolide synthesis: Synthesis of a C16-C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spisoacetal moiety

The C16-C28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration.