112348-03-5

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 112635-76-4 (+)-(R)-ethyl 3,4-dihydroxybutanoate 

Downstream Products

• 251641-49-3 ((2R,4S,6R)-2-Phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-acetaldehyde 
• 251641-48-2 ((2R,4S,6R)-2-Phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-acetic acid tert-butyl ester 
• 251641-59-5 [(2S,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde 
• 251641-58-4 2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol 
• 251641-60-8 1-[(2S,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one 
• 251641-57-3 (2R,4S,6R,8R,10S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undecane 
• 251641-50-6 (R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1-((2R,4R,6R)-2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-octan-4-one 
• 251641-51-7 (Z)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-6-(4-methoxy-benzyloxy)-1-((2R,4S,6R)-2-phenyl-6-triisopropylsilanyloxymethyl-[1,3]dioxan-4-yl)-oct-3-en-2-one 
• 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 

Relevant academic research and scientific papers

Synthesis of the C1-C28 Portion of Spongistatin 1 (Altohyrtin A)

A synthetic approach was developed to the C1-C28 subunit of spongistatin 1 (altohyrtin A, 65). The key step was the coupling of the AB and CD spiroketal moieties via an anti-aldol reaction of aldehyde 62 and ethyl ketone 57. The development of a method for the construction of the AB spiroketal fragment is described and included the desymmetrization of C2-symmetric diketone 10 and the differentiation of the two primary alcohols of 16. Further elaboration of this advanced intermediate to the desired aldehyde 62 included an Evans' syn-aldol reaction and Tebbe olefination. The synthesis of the CD spiroketal fragment 56 involved the ketalization of a triol-dione, generated in situ by deprotection of 45, to provide a favorable ratio (6-7:1) of spiroketal isomers 46 and 47, respectively. The overall protecting group strategy, involving many selective manipulations of silyl protecting groups, was successfully developed to provide the desired C1-C28 subunit of spongistatin 1 (altohyrtin A) (65).