279227-20-2

Upstream product

• 81678-40-2 (2S)-5-(benzyloxy)-2-methylpentan-1-ol 
• 64740-39-2 5-benzyloxypentanoic acid 
• 250679-54-0 (4S)-4-benzyl-3-[(2S)-5-(benzyloxy)-2-methylpentanoyl]-1,3-oxazolan-2-one 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 142945-19-5 (4S)-4-benzyl-3-[5-(benzyloxy)pentanoyl]oxazolidin-2-one 
• 100-44-7 benzyl chloride 
• 851955-70-9 (2S)-5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylpentanamide 
• 851955-69-6 5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpentanamide 
• 371784-89-3 (S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol 
• 888484-13-7 ethyl (S)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpentanoate 

Downstream Products

• 279227-04-2 (4R,5S,6S)-9-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-5-hydroxy-2,4,6-trimethylnonan-3-one 
• 844439-31-2 (R)-4-Benzyl-3-((2R,3S,4S)-7-benzyloxy-3-hydroxy-2,4-dimethyl-heptanoyl)-oxazolidin-2-one 
• 851955-71-0 (2R,3S,4S)-7-Benzyloxy-3-hydroxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide 
• 865535-29-1 (E)-(6R,7S,8S)-11-Benzyloxy-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-undec-2-enoic acid methyl ester 
• 844439-33-4 (R)-4-Benzyl-3-[(2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 844439-34-5 (R)-4-Benzyl-3-[(2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-7-iodo-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 844439-32-3 (R)-4-Benzyl-3-[(2R,3S,4S)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 844439-35-6 (R)-4-Benzyl-3-[(8Z,12E)-(2R,3S,4S,11S)-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dienoyl]-oxazolidin-2-one 
• 844439-45-8 (R)-4-Benzyl-3-[(8Z,12E)-(2R,3S,4S,11S)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-11-triethylsilanyloxy-trideca-8,12-dienoyl]-oxazolidin-2-one 
• 923956-04-1 (4S,7R,8S,9S)-12-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-dodec-1-en-6-one 
• 923956-36-9 C₂₉H₅₀O₄Si 
• 1159576-53-0 (4S,Z)-1-benzyloxy-4-methyl-5-octene 
• 1002320-64-0 C₁₄H₂₂O₂ 

Relevant academic research and scientific papers

The total synthesis and biological assessment of trans-epothilone A

The total synthesis of (12S,13S)-trans-epothilone A (1a) was achieved based on two different convergent strategies. In a first-generation approach, construction of the C(11)-C(12) bond by Pd0-catalyzed Negishi-type coupling between the C(12)-to-C(15) trans-vinyl iodide 5 and the C(7)-to-C(11) alkyl iodide 4 preceded the (nonselective) formation of the C(6)-C(7) bond by aldol reaction between the C(7)-to-C(15) aldehyde 25 and the dianion derived from the C(1)-to-C(6) acid 3. The lack of selectivity in the aldol step was addressed in a second-generation approach, which involved construction of the C(6)-C(7) bond in a highly diastereoselective fashion through reaction between the acetonide-protected C(l)-to-C(6) diol 31 ('Schinzer's ketone') and the C(7)-to-C(11) aldehyde 30. As part of this strategy, the C(11)-C(12) bond was established subsequent to the critical aldol step and was based on B-alkyl Suzuki coupling between the C(1)-to-C(11) fragment 40 and C(12)-to-C(15) trans-vinyl iodide 5. Both approaches converged at the stage of the 3-O, 7-O-bis-TBS-protected seco acid 27, which was converted to trans-deoxyepothilone A (2) via Yamaguchi macrolactonization and subsequent deprotection. Stereoselective epoxidation of the trans C(12)-C(13) bond could be achieved by epoxidation with Oxone in the presence of the catalyst 1,2:4,5-di-O-isopropylidene-L-erythro-2,3-hexodiuro-2,6-pyranose (42a), which provided a 8:1 mixture of 1a and its (12R,13R)-epoxide isomer 1b in 27% yield (54% based on recovered starting material). The absolute configuration of 1a was established by X-ray crystallography. Compound 1a is at least equipotent with natural epothilone A in its ability to induce tubulin polymerization and to inhibit the growth of human cancer cell lines in vitro. In contrast, the biological activity of 1b is at least two orders of magnitude lower than that of epothilone A or 1a.

Total synthesis of s (+)-curcuphenol, s (+)-curcuquinone and s (+)-curcuhydroquinone

A synthesis of (-)-curcuphenol, (-)-curcuquinone and (-)-curcuhydroquinone from o-valerolactone is described. The key steps include an Evans asymmetric methylation of 5-(benzyloxy)pentanoic acid (5), an oxidative aromatization of enone (11) and a regioselective oxidation of the phenol to o-quinone derivative with bis(trifluoro acetate)iodobenzene.

Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters

The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on

EPOTHILONE ANALOGUES

Epothilone analogues include a molecular scaffold which holds at least one segment of epothilone in a predetermined orientation and which rigidities a region between the macrolactone ring and the aromatic side-chain.

Total synthesis of 12,13-desoxyepothilone B (Epothilone D)

A highly convergent total synthesis of 12,13-desoxyepothilone B (4, Epothilone D) is described involving the coupling of vinyl iodide (5) and olefin (6). Key steps in the synthesis are the introduction of chirality at C15 via highly enantioselective lipas

Total synthesis of halipeptins: Isolation of halipeptin D and synthesis of oxazoline halipeptin analogues

The isolation from the marine sponge Leiosella cf. arenifibrosa and structural elucidation of halipeptin D (5). a relative of the previously isolated halipeptins A-C (1-3), is described along with the total synthesis of a number of oxazoline analogues (7a

Synthesis of 4-aza analogs of epothilone D

An efficient synthesis of epothilone D analogs of type 1 has been developed, which is based on a highly diastereoselective Evans aldol reaction as one of the key steps. A profound difference in the relative stabilities of TBS-protecting groups on C7-O and C15-O was observed between secondary and primary amide groups at C5-N4. Although modeling studies had suggested analogs of type 1 to assume a conformation similar to the NMR-derived conformation of tubulin-bound epothilone A, compounds 1a-d were found to be significantly less active than the parent compound epothilone D.