237735-60-3

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 237735-59-0 methyl (4E,3S)-6-[(t-butyldimethylsilyl)oxy]-4-methyl-3-hydroxy-4-hexenoate 

Downstream Products

• 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 
• 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 
• 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 
• 544429-53-0 (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 
• 237735-42-1 (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene 
• 237735-43-2 (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-ol 
• 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.