887612-10-4

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 1245726-33-3 ethyl 3-((2R,3S,6S,8S)-8-[(S)-4-hydroxy-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propanoate 
• 256464-87-6 (3S,4R)-7-(benzyloxy)-3-methylhept-1-en-4-ol 
• 887612-08-0 (S)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-tetrahydro-pyran-2-one 
• 256464-89-8 (3S,4R)-4,7-Bis-benzyloxy-3-methyl-heptane-1,2-diol 
• 887612-21-7 C₂₂H₂₆Br₂O₂ 
• 256464-88-7 C₂₂H₂₈O₂ 
• 256464-90-1 (2R,3R)-3,6-Bis-benzyloxy-2-methyl-hexanal 

Downstream Products

• 887612-26-2 2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione 
• 1391853-35-2 tert-butyl {(S)-4-[(2S,6S,8R,9S)-8-(3-iodopropyl)-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2-methylbutoxy}diphenylsilane 
• 115566-02-4 bistramide A 

Relevant academic research and scientific papers

Total synthesis of bistramide A and its 36(Z) isomers: Differential effect on cell division, differentiation, and apoptosis

The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product. Copyright

Synthesis of the spiroketal fragment of bistramide A via an exocyclic enol ether

An efficient synthesis of the spirocyclic fragment 1 of bistramides is reported. An olefination reaction of lactone 4 with sulfone 5 gave the enol ether 3, which upon cyclization in acidic media provided the spiroketal ring system. This compound was then converted into the C19-C36 fragment of the bistramides via successive Julia-Kocienski and Horner-Emmons olefinations.

Enantioselective total synthesis of bistramide A

The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright