169897-93-2

Upstream product

• 169897-88-5 [4S,3(2S)]-4-benzyl-3-(4-benzyloxy-2-allyl-1-butanoyl)-2-oxazolidinone 
• 169897-87-4 [4S]-4-benzyl-3-(4-benzyloxy-1-butanoyl)-2-oxazolidinone 
• 544429-65-4 C₁₄H₁₈O₅ 
• 100-39-0 benzyl bromide 
• 10385-30-5 4-(benzyloxy)butanoic acid 
• 169897-90-9 (3S-hydroxymethyl-1-(benzyloxy))-5-hexene 

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 
• 544429-45-0 (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid 
• 544429-29-0 ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzyloxy)ethyl]-9-[(2'-benzothiazolyl)sulfonyl]-2-nonenoate 
• 544429-30-3 ethyl (2E,5S,7R,8S)-8-methyl-7-benzyloxy-5-[2-(benzylloxy)ethyl]-9-(methanesulfonyl)-2-nonenoate 
• 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 
• 237735-61-4 (2R,3R,5S)-1-[(triisopropylsilyl)oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol 
• 169898-01-5 ethyl (2E,5S,7R,8R)-9-[[t-butyldiphenylsilyl]oxy]-8-methyl-7-benzyloxy-5-[2-(benzyloxy)ethyl]-2-nonenoate 
• 169898-00-4 (3S,5R,6R)-7-[[t-butyldiphenylsilyl]oxy]-6-methyl-5-benzyloxy-3-[2-(benzyloxy)ethyl]-heptanal 
• 169897-99-8 (2R,3R,5S)-(t-butyl)-[2-methyl-3-(benzyloxy)-5-[2-(benzyloxy)ethyl]-7-octenyloxy]diphenylsilane 
• 169897-96-5 [4S,3(2S,3R,5S)]-4-benzyl-3-(5-allyl-6-benzyloxy-3-hydroxy-2-methyl-1-heptanoyl)-2-oxazolidinone 
• 169897-98-7 (2R,3R,5S)-1-[[t-butyldiphenylsilyl]-oxy]-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-3-ol 
• 169898-02-6 ethyl (2E,5S,7R,8R)-9-hydroxy-8-methyl-7-benzyloxy-5-[2-(benzyloxy)ethyl]-2-nonenoate 
• 169897-97-6 (2R,3R,5S)-2-methyl-5-[2-(benzyloxy)ethyl]-7-octene-1,3-diol 
• 169897-95-4 (3S)-[2-(benzyloxyethyl)]-5-hexenal 

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.

Rhizoxin synthetic studies. 1. Synthesis of the right hand [C(1) to C(9)]portion via a "pinwheel" approach

A concise synthetic approach to the C(1) - C(9) fragment of the antitumor macrolide rhizoxin via a three-fold pseudosymmetric intermediate is described. The preparation (from readily available γ-butyrolactone) includes both an asymmetric allylation and an