357419-52-4

Upstream product

• 484664-27-9 (2S)-1-benzyloxy-5-trimethylsilanyl-pent-4-yn-2-ol 
• 357419-50-2 (2S)-1-O-benzyl-2-methoxypent-4-yn-1-ol 
• 263543-12-0 (4R,2'R,3'S,4'S,5'R,7'R)-4-benzyl-3-(7'-tert-butyldimethylsilyloxy-3',5'-dihydroxy-8'-methoxy-2',4'-dimethyl-1'-oxooctyl)-1,3-oxazolidin-2-one 
• 263543-11-9 (4R,2'R,4'S,5'R,7'R)-4-benzyl-3-(7'-tert-butyldimethylsilyloxy-5'-hydroxy-8'-methoxy-2',4'-dimethyl-1',3'-dioxooctyl)-1,3-oxazolidin-2-one 
• 916218-12-7 (2R,3S,4S,5R,7R)-7-(t-butyldimethylsilyloxy)-3,5-dihydroxy-N,8-dimethoxy-N,2,4-trimethyloctanamide 
• 918148-56-8 3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-butyric acid methyl ester 
• 263543-10-8 (R)-3-(tert-butyldimethylsilyloxy)-4-methoxybutanal 
• 166539-00-0 (3R)-3-hydroxy-4-methoxybutyric acid methylester 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 41051-15-4 4-methoxyacetoacetic acid methylester 

Downstream Products

• 357419-67-1 Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester 
• 357419-66-0 (2S,3R,4S,5S,6R)-2-((E)-(S)-5-Benzyloxy-4-methoxy-pent-1-enyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran 

Relevant academic research and scientific papers

Apoptolidinone A: Synthesis of the apoptolidin a aglycone

An efficient stereocontrolled synthesis of apoptolidinone A, the aglycone of apoptolidin A is described. The synthetic strategy relies on a cross coupling between C11/C12 of a northern half (C1-C11) and a southern part (C12-C28) followed by a ring-size selective macrolactonization. Key steps for the introduction of the southern half stereocenters are a stereoselective aldol reaction, a substrate controlled dihydroxylation and a chelation-controlled Grignard/aldehyde addition. The conjugated triene of the northern half was built up successively by E-selective Wittig reactions. L-Malic acid was chosen as the chiral pool source for the C8/C9 stereocenters. The final cleavage of the silyl ethers and the conversion of the C21 methyl ketal into the hemiketal was achieved by HF-pyridine.