128271-10-3

Upstream product

• 185300-82-7 (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 104486-82-0 (R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one 
• 905589-59-5 (3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate 
• 185300-90-7 (2R,3R)-3-Benzyloxy-2-methyl-butan-1-ol 
• 185300-86-1 (2S,3R)-3-Benzyloxy-2-methyl-butyraldehyde 
• 933731-96-5 (3,4-dimethoxybenzyloxy) acetic acid 
• 1025909-69-6 (3,4-Dimethoxy-benzyloxy)-acetyl chloride 
• 185300-91-8 (3,4-Dimethoxy-benzyloxy)-acetic acid methyl ester 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 104486-86-4 (+)-methyl pederate 
• 185300-95-2 (4R,5R,6R)-6-Benzyloxy-5-methyl-hept-1-en-4-ol 
• 185300-92-9 (2S,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-6-methyl-octane-1,3-dione 
• 185300-83-8 (S)-3-[(2S,3R,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-3-hydroxy-6-methyl-octanoyl]-4-isopropyl-oxazolidin-2-one 
• 1054698-71-3 (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one 

Downstream Products

• 128271-11-4 (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide 
• 128271-11-4 (S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide 
• 128271-12-5 Acetic acid (S)-3-{(4S,4aS,6R,8S,8aR)-4-[(S)-2-(3,4-dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetylamino]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-2-methoxy-propyl ester 
• 128271-12-5 Acetic acid (S)-3-{(4R,4aS,6R,8S,8aR)-4-[(S)-2-(3,4-dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetylamino]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-2-methoxy-propyl ester 
• 115185-92-7 mycalamide A 
• 185300-82-7 (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Highly diastereoselective synthesis of pederic acid derivatives

A highly diastereoselective synthesis of methyl pederate (2) is described. A critical feature of the successful route is the introduction of the key C(7)-stereocenter at the stage of 4 via an enantioselective, syn-selective aldol reaction of aldehyde 5 and the chiral acyl oxazolidinone 6. Aldehyde 5, in turn, was prepared from the readily available aldol derivative 7 via a chelate-controlled reaction with allyltrimethylsilane. Intermediate 4 was elaborated to 2 via the intermediacy of 7-O-(3,4-dimethoxybenzyl)pederic acid (3), an intermediate in Kishi's syntheses of mycalamides A and B and onnamide A, by way of methyl pyranoside 16 and the fully protected pederic acid derivative 11.

Total Synthesis of Mycalamides A and B

A total synthesis of mycalamides A (1) and B (2) was accomplished in an enantiomerically pure form, establishing unambiguously their absolute configuration.