302355-98-2

Upstream product

• 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 
• 139403-50-2 (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one 
• 207276-55-9 (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 210691-72-8 (R)-4-[(1R,2R)-2-(4-Chlorobenzoyloxy)-1-methylpropyl]dihydrofuran-2(2H)-one 
• 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 
• 210691-86-4 (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 
• 210691-88-6 (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 
• 210691-73-9 (3S,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(phenylselanylmethyl)hexanoic acid 
• 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 
• 210691-87-5 (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 
• 210691-71-7 (3R,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(triphenylmethyoxymethyl)hexanoic acid 
• 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 
• 218965-72-1 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 
• 218965-70-9 (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 

Relevant academic research and scientific papers

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.

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.