157758-33-3

Upstream product

• 38435-08-4 trimethyl 3-(phenylsulfonyl)orthopropionate 
• 157758-29-7 (R)-2-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-oxirane 
• 157758-39-9 Methanesulfonic acid (1S,3S,4S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-5-(4-methoxy-benzyloxy)-4-methyl-pentyl ester 
• 157758-38-8 1-[(2S,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-2-methyl-hexyloxymethyl]-4-methoxy-benzene 
• 157758-32-2 (2S,4S,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-6-(4-methoxy-benzyloxy)-5-methyl-hexan-2-ol 
• 157758-31-1 C₃₁H₅₀O₃Si₂ 
• 157758-37-7 (3S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hept-1-en-4-ol 
• 180592-87-4 (4R,6S)-4-Iodomethyl-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxan-2-one 
• 180592-88-5 (2S,3S)-4-(4-Methoxy-benzyloxy)-3-methyl-1-(R)-oxiranyl-butan-2-ol 
• 180592-86-3 (2S,3S)-1-(4-methoxybenzyloxy)-2-methylhex-5-en-3-ol 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 

Downstream Products

• 157758-34-4 (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester 
• 157811-05-7 (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester 
• 157811-04-6 {(2R,6S)-6-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde 
• 175612-35-8 C₆₀H₁₀₄O₁₂Si₂ 
• 175612-36-9 C₅₉H₁₀₂O₁₂Si₂ 
• 180593-05-9 C₅₉H₁₀₀O₁₁Si₂ 
• 175612-30-3 C₆₂H₁₁₂O₁₁Si₃ 
• 175612-34-7 C₅₇H₁₀₀O₁₁Si₂ 
• 175612-33-6 C₅₇H₁₀₂O₁₁Si₂ 
• 180592-94-3 Benzoic acid (2S,3S)-4-{(2S,6R)-6-[(E)-(S)-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxycarbonyl-hex-4-enyl]-3,6-dihydro-2H-pyran-2-yl}-3-methoxy-2-methyl-butyl ester 
• 180592-93-2 Benzoic acid (2S,3S)-4-[(2S,6R)-6-((E)-(S)-2-hydroxy-5-methoxycarbonyl-hex-4-enyl)-3,6-dihydro-2H-pyran-2-yl]-3-methoxy-2-methyl-butyl ester 
• 180592-91-0 Benzoic acid (2S,3S)-3-methoxy-2-methyl-4-[(2S,6R)-6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-butyl ester 
• 180592-90-9 Benzoic acid (2S,3S)-4-((2S,6R)-6-allyl-3,6-dihydro-2H-pyran-2-yl)-3-methoxy-2-methyl-butyl ester 

Relevant academic research and scientific papers

Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A

The total synthesis of swinholide A (1) has been accomplished via key intermediate aldehyde 12 (Fig. 3), whose construction started from L-rhamnose (18), epoxide 21, and phenylsulfone orthoester 22, and proceeded through an Enders asymmetric alkylation (16 + 17 -> 15), a Ghosez cyclization (21 + 22 -> 20), and a Corey-Sharpless coupling reaction (13 + 14 -> 12).Elaboration of compound 12 along slightly different pathways culminated in the synthesis of carboxylic acid 10 and hydroxy compound 11, whose union by an esterification reaction, followed by ring closure of the subsequently derived hydroxy acid under Yamaguchi conditions, led to swinholide A (1) upon deprotection.The chemistry developed also allowed the total synthesis of preswinholide A methyl ester (7), preswinholide A (8), and hemiswinholide A (78).Keywords: natural products; swinholide A; total syntheses

A Convergent Approach to Swinholide A. Stereoselective Construction of the C3-C17 Fragment of Swinholide A

A strategy for a total synthesis of the cytotoxic dimeric macrolide swinholide A (1, Scheme 1) is outlined and a stereoselective construction of the suitably functionalized C3-C17 fragment 4, starting with building blocks 6, 7, 9 and 10 is described.