405176-41-2

Upstream product

• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 389123-35-7 {2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 
• 389123-22-2 (2R,6R)-2-((E)-2-Bromo-propenyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-4-one 
• 389123-39-1 [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene 
• 389123-37-9 5-{2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethanesulfonyl}-1-phenyl-1H-tetrazole 
• 389123-41-5 (Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enal 
• 389123-38-0 (Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid ethyl ester 
• 389123-23-3 2-[(2S,6R)-6-((E)-2-Bromo-propenyl)-4-methylene-tetrahydro-pyran-2-yl]-ethanol 
• 389123-24-4 (Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol 
• 405176-39-8 (R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane 
• 197520-87-9 (R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 3095-95-2 diethylphosphonoacetic acid 
• 405176-40-1 (E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol 

Downstream Products

• 405176-38-7 (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester 
• 405176-42-3 (2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethyl)-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one 
• 405176-46-7 (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one 
• 405176-43-4 (2E,8E,10Z,14E)-(1R,5R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione 
• 405176-45-6 (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester 

Relevant academic research and scientific papers

Total synthesis of (+)-dactylolide.

[reaction: see text] The total synthesis of the new cytotoxic marine macrolide (+)-dactylolide (1) has been achieved in nine steps from known vinyl bromide (-)-AB. In addition, (+)-zampanolide (2) has been converted to (+)-dactylolide (1) via thermolysis.

Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy

The first total syntheses of (+)-zampanolide (1) and (+)-dactylolide (2), members of a new class of tumor cell growth inhibitory macrolides, have been achieved. Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal. The complete relative and absolute stereochemistries for both (+)-zampanolide and (+)-dactylolide were also assigned, albeit tentatively in the case of (+)-zampanolide (1).