218965-70-9

Upstream product

• 210691-71-7 (3R,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(triphenylmethyoxymethyl)hexanoic acid 
• 210691-87-5 (1R,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-10-methoxy-9,9-dimethyl-8-(3-phenylselanylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 210691-84-2 (1S,5R,6R,8R)-5-(tert-Butylcarbonyloxy)methyl-8-(3-chloropropyl)-9,9-dimethyl-2,4,7-trioxabicyclo[4.4.0]decan-10-one 
• 210691-73-9 (3S,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(phenylselanylmethyl)hexanoic acid 
• 210691-88-6 (1R,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 210691-86-4 (1R,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-8-(3-chloropropyl)-10-methoxy-9,9-dimethyl-2,4,7-trioxabicyclo[4.4.0]decane 
• 210691-85-3 (1S,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-8-(3-chloropropyl)-9,9-dimethyl-2,4,7-trioxabicyclo[4.4.0]decan-10-ol 
• 210691-72-8 (R)-4-[(1R,2R)-2-(4-Chlorobenzoyloxy)-1-methylpropyl]dihydrofuran-2(2H)-one 
• 1666-13-3 diphenyl diselenide 
• 289666-93-9 (-)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate 
• 289667-10-3 (+)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxy-heptanoate 
• 289667-09-0 (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol 
• 289666-87-1 (+)-(2S,3R,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 
• 289667-02-3 (+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene 

Downstream Products

• 218965-74-3 7-O-Benzoyltheopederin D 
• 302355-98-2 17-epi-7-O-Benzoyltheopederin D 
• 218965-71-0 Benzoic acid (S)-((4S,4aS,6R,8S,8aR)-6-allyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl)-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester 
• 218965-73-2 Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 218965-72-1 Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester 

Relevant academic research and scientific papers

Convergent total synthesis of (+)-mycalamide A

The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.

Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin

The synthesis of mycalamide B, theopederin D and pederin, which are antitumour agents was discussed. All three compounds were prepared from 6-lithio-2,3-dimethyl-4-phenylselenomethyl-3,4-dihydro-2H-pyran and 2-(3-chloropropyl)-3,3-dimethyl-3,4-dihydro-2H-pyran-4-one. Ground state conformational models were proposed to explain the stereoselectivity of the reactions. The absolute and relative stereochemistry of the compounds has been established by X-ray crystallography and NMR studies.

A synthesis of theopederin D and a formal synthesis of pederin

Theopederin D, a cytotoxic metabolite from a sponge of the genus Theonella, was synthesised in 14 steps (11.1% overall yield) from two advanced intermediates previously used in a synthesis of mycalamide B. A formal synthesis of pederin from similar intermediates is also reported.