357419-51-3

Upstream product

• 484664-27-9 (2S)-1-benzyloxy-5-trimethylsilanyl-pent-4-yn-2-ol 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 357419-50-2 (2S)-1-O-benzyl-2-methoxypent-4-yn-1-ol 

Downstream Products

• 357419-53-5 (2S,3R,4S,5R,6R)-2-((E)-(S)-5-Benzyloxy-4-methoxy-pent-1-enyl)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol 
• 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 
• 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 

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.