163216-03-3

Upstream product

• 194610-23-6 (R)-tert-butyl((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)diphenylsilane 
• 92817-88-4 (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 
• 95514-04-8 (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 95514-03-7 (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 
• 558-13-4 carbon tetrabromide 
• 95514-04-8 (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 1023949-14-5 (5E,7E)-(2S,3R,4S,9R)-10-(tert-butyldiphenylsiloxy)-3-methoxy-2,4,6,9-tetramethyldeca-5,7-dien-1-ol 
• 1234628-02-4 C₃₇H₄₆O₄Si 
• 1293306-30-5 ((R)-4-iodo-2-methylbut-3-ynyloxy)(tert-butyl)diphenylsilane 
• 1437785-07-3 (1R,2R)-2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-1-(furan-2-yl)-cyclopentanol 
• 1437785-08-4 (1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one 
• 1437785-09-5 (1R,5R,7R)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]decan-10-one 
• 1437785-10-8 ((R)-2-((1R,5S,7R)-7-allyl-6-oxaspiro[4.5]decan-1-yl)propoxy)-(tert-butyl)diphenylsilane 
• 1437785-11-9 tert-butyldiphenyl[(2R)-2-[(1R,5S,7S)-7-propyl-6-oxaspiro[4.5]decan-1-yl]propoxy]silane 
• 1437785-12-0 (E)-ethyl 4-((1R,5S,7R)-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]decan-7-yl)-2-methylbut-2-enoate 
• 1437785-04-0 (R)-2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentanone 
• 1437785-05-1 (S)-2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentanone 
• 1437785-03-9 (R)-2-(1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopent-2-enone 
• 1293306-32-7 ((R,Z)-4-iodo-2-methylbut-3-enyloxy)(tert-butyl)diphenylsilane 
• 955959-44-1 ((2R,6R)-7-benzyloxy)-2,6-dimethylhept-3-yn-1-ol 

Relevant academic research and scientific papers

Quinocidin, acytotoxic antibiotic with anunusual 3,4-dihydroquinolizinium ring and michael acceptor reactivity toward thiols

Cytotoxicity-guided fractionation of the culture broth of Actinomadura sp. TP-A0019 led to the isolation of quinocidin (1), acytotoxic antibiotic with an unusual 3,4-dihydroquinolizinium ring. The structural assignment was made on the basis of high-field NMR experiments and chemical synthesis. Comparison ofthe spectral properties of 1 with those of its synthetic counterparts revealed that 1 is aracemic mixture of two enantiomers, which showed similar cytotoxicity against HeLa-S3 cells. Nucleophile-trap-ping experiments demonstrated that 1 captured 2-mer-captoethanol and N-acetyl-l-cysteine by means of aMi-chael addition-type reaction, but was inert toward 2-ami-noethanol and glycolic acid. Notably, the addition of 1 to thiols proceeded smoothly in neutral aqueous media at room temperature. In view of the thiol-trapping ability and the unusual structure, 1 provides aunique scaffold for designing drug leads and protein-labeling probes.

Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The

Convergent approach to complex spirocyclic pyrans: Practical synthesis of the oxa-pinnaic acid core

The enantioselective synthesis of the oxa-pinnaic acid framework has been achieved through internal asymmetric induction. The synthetic strategy pursued illustrates the adaptability of the Achmatowicz oxidative rearrangement for the synthesis of complex spirocyclic pyrans starting from tertiary alcohols. The Royal Society of Chemistry.

A general synthetic approach to the amnesic shellfish toxins: Total synthesis of (-)-isodomoic acid B, (-)-isodomoic acid E and (-)-isodomoic acid F

The alkynylpyrrolidine 4 was made via a dearomatising cyclisation of an aromatic amide, and was elaborated by stannylcupration and palladium-catalysed coupling to achieve the first total synthesis of three members of the isodomoic acid family; the same alkyne can be envisaged as a precursor to several more of this class of amnesic shellfish toxins. The Royal Society of Chemistry.

Total synthesis of (-)-amphidinolide E

The unique structural features of the cytotoxic marine macrolide (-)-amphidinolide E make it an intriguing synthetic target. Its total synthesis has now been completed by employing a radical cyclization of a β-alkoxy acrylate to form the oxolane ring, a Kocienski-Julia olefination to create the E C=C bond, and a lactonization reaction to close the macrocyclic ring. (Chemical Equation Presented).