237735-43-2

Upstream product

• 113732-84-6 2-methyl-1,3-oxazole-4-carbaldehyde 
• 139630-90-3 (1'E,3'E)-2-methyl-4-(2'-methyl-5'-oxo-1',3'-pentadienyl)-oxazole 
• 139630-93-6 (1'E,3'E)-4-(5'-Hydroxy-2'-methyl-1',3'-pentadienyl)-2-methyloxazole 
• 144950-82-3 (E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal 
• 141567-53-5 4-hydroxymethyl-2-methyloxazole 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 544429-48-3 (E)-(2S,3S,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-5-triisopropylsilanyloxy-3-trimethylsilanyloxy-oct-6-enoic acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester 
• 544429-47-2 (E)-(2S,3S,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-5-triisopropylsilanyloxy-oct-6-enoic acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester 
• 544429-35-8 (1'E,3'E)-4-(4'-(ethoxycarbonyl)-2'-methyl-1',3'-butadienyl)-2-methyloxazole 
• 544429-53-0 (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-8-ol 
• 237735-40-9 (1E,3E,5E,12E)-(8S,9S,11S)-14-(tert-Butyl-dimethyl-silanyloxy)-2,6,8,12-tetramethyl-1-(2-methyl-oxazol-4-yl)-11-triisopropylsilanyloxy-9-trimethylsilanyloxy-tetradeca-1,3,5,12-tetraen-7-one 
• 237735-30-7 (2E,4S,6S,7S,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-6-hydroxy-3,7,9,13-tetramethyl-14-(2'-methyl-4'-oxazolyl)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-8-one 
• 237735-26-1 (2E,4S,6S,7R,8RS)-1-[(t-butyldimethylsilyl)oxy]-9-(diethylphosphono)-3,7-dimethyl-4-[(triisopropylsilyl)oxy]-6-[(trimethylsilyl)oxy]-2-decaen-8-one 
• 237735-39-6 (2E,4S,6S,7R,8RS)-1-[(t-butyldimethylsilyl)oxy]-9-(diethylphosphono)-3,7-dimethyl-4-[(triisopropylsilyl)oxy]-6-[(trimethylsilyl)oxy]-2-decaen-8-ol 

Downstream Products

• 237735-34-1 4-nitro-benzoic acid 1-{7-[6-(tert-butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester 
• 544429-56-3 4-nitro-benzoic acid 1-{7-[4-(3-ethoxycarbonyl-allyl)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester 
• 237735-31-8 (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al 

Relevant academic research and scientific papers

Enantioselective total synthesis of the antitumor macrolide rhizoxin D

The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)-C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from γ-butyrolactone. The central core of rhizoxin D was prepared via a chiral resolution/asymmetric aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepared from serine in six steps. The unification of the left and right wings of the molecule was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner-Emmons olefination at the C(2)-C(3) olefin.

The enantioselective total synthesis of the antitumor macrolide natural product rhizoxin D

A convergent, enantioselective total synthesis of rhizoxin D (didesepoxy-rhizoxin), a potent antitumor natural product, was achieved via three critical olefinations, including a Horner-Emmons macrocyclization.