625124-80-3

Upstream product

• 625124-70-1 (4R)-5-benzyloxy-4-triethylsilanyloxypentan-2-one 
• 625124-68-7 tert-butyl (2S,4R,6S)-2-(4-methoxyphenyl)-6-(2-oxoethyl)-[1,3]dioxan-4-ylacetate 
• 862465-84-7 tert-butyl 2-((6S,4R)-6-{[1,1-bis(1-methylethyl)-2-methyl-1-silapropoxy]methyl}-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)acetate 
• 625125-24-8 tert-butyl (3R,5S)-[6-allyl-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]acetate 
• 625124-74-5 tert-butyl (3R,5S)-3,5-dihydroxy-6-triisoppropylsilanyloxyhexanoate 
• 1026478-50-1 [(2S,4R,6S)-6-Iodomethyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 625124-76-7 tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate 
• 604775-07-7 (2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol 
• 540-88-5 acetic acid tert-butyl ester 

Downstream Products

• 625124-66-5 [(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 625124-82-5 [(2R,4S,6R,8R)-8-benzyloxymethyl-4-hydroxy-10-oxo-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester 
• 625125-33-9 [(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester 
• 625125-02-2 [(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester 

Relevant academic research and scientific papers

A Second-Generation Synthesis of the C1-C28 Portion of the Altohyrtins (Spongistatins)

A practical second-generation synthesis of an advanced intermediate in our total synthesis of altohyrtin C (spongistatin 2) has been developed. A new approach to the C1-C15 (AB) portion features a vinyllithium addition to an aldehyde followed by a palladium-catalyzed allylic reduction to install the troublesome C13-C15 segment. Our general approach to the C16-C28 (CD) spiroketal has been retained, but some improvements have been made. Most notably, the kinetically controlled CD-spiroketalization reaction now proceeds in high yield with excellent diastereoselection. This new strategy uses the anti-aldol coupling used in our first-generation synthesis to join AB and CD fragments. A total of 9.6 g of intermediate 57 has been produced using this improved route.