237735-34-1

Upstream product

• 237735-27-2 2-{(S)-2-[(2R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-propane-1-sulfonyl}-benzothiazole 
• 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 
• 144950-82-3 (E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal 
• 141567-53-5 4-hydroxymethyl-2-methyloxazole 
• 169897-93-2 2S-[2-(benzyloxy)ethyl]-4-pentenal 
• 169897-90-9 (3S-hydroxymethyl-1-(benzyloxy))-5-hexene 
• 169897-95-4 (3S)-[2-(benzyloxyethyl)]-5-hexenal 
• 169897-97-6 (2R,3R,5S)-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-1,3-diol 
• 169897-96-5 [4S,3(2S,3R,5S)]-4-benzyl-3-(5-allyl-6-benzyloxy-3-hydroxy-2-methyl-1-heptanoyl)-2-oxazolidinone 
• 237735-46-5 [4R,6R,6(1R)]-4-allyl-6-[(1-methyl-2-hydroxy)ethyl]-4H-pyran-2-one 
• 237735-32-9 [4R,6R,6(1R)]-4-allyl-6-[1-methyl-2-(methanesulfonyl)ethyl]-4H-pyran-2-one 
• 237735-59-0 methyl (4E,3S)-6-[(t-butyldimethylsilyl)oxy]-4-methyl-3-hydroxy-4-hexenoate 
• 237735-45-4 [4R,6R,6(1R)]-4-allyl-6-[1-methyl-2-((triisopropylsilyl)oxy)ethyl]-4H-pyran-2-one 
• 237735-47-6 (4R,6R)-4-Allyl-6-[(S)-2-(benzothiazol-2-ylsulfanyl)-1-methyl-ethyl]-tetrahydro-pyran-2-one 

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.