389086-01-5

Upstream product

• 389086-10-6 (Z)-(3S,7R)-9-Benzyloxy-3-(4-methoxy-benzyloxy)-7-triethylsilanyloxy-1-[2-(4-triethylsilanyloxy-butyl)-[1,3]dithian-2-yl]-non-5-en-4-one 
• 389086-03-7 (S)-2,2-diethyl-5-(2-{2-[4-(tetrahydropyran-2-yloxy)butyl]-1,3-dithian-2-yl}ethyl)-1,3-dioxolane 
• 389086-15-1 (4R)-4-benzyl-3-(4-benzyloxy-1-oxobutyl)-2-oxazolidinone 
• 389086-18-4 (R)-4-benzyloxy-2-triethysilyloxy-1-butanol 
• 389085-92-1 (R)-4-benzyloxy-2-(triethysilyloxy)butanal 
• 111741-88-9 5-(1',3'-dithian-2'-yl)-1-(2-tetrahydropyranyloxy)pentane 
• 500318-59-2 (3S,7R)-9-benzyloxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}-5-nonen-4-one 
• 389086-12-8 2-[(3S,4R,7S)-9-benzyloxy-4-(tert-butyldimethylsilyl)oxy-3-(4-methoxybenzyl)oxy-4-methyl-7-(triethylsilyloxy)nonyl]-2-[4-(triethylsilyloxy)butyl]-1,3-dithiane 
• 500318-79-6 Acetic acid (S)-1-((R)-3-benzyloxy-1-triethylsilanyloxy-propyl)-4-(4-methoxy-benzyloxy)-3-oxo-6-[2-(4-triethylsilanyloxy-butyl)-[1,3]dithian-2-yl]-hexyl ester 
• 389086-11-7 (3S,4R,7S)-9-benzyloxy-3-(4-methoxybenzyl)oxy-4-methyl-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-ol 
• 389086-23-1 1-{2-[(3S,4R,7S)-9-benzyloxy-4-(tert-butyldimethylsilyl)oxy-3-(4-methoxybenzyl)oxy-4-methyl-7-(triethylsilyloxy)nonyl]-1,3-dithian-2-yl}-4-hepten-6-one 
• 389086-09-3 (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one 
• 389086-13-9 4-{2-[(3S,4R,7S)-9-benzyloxy-4-(tert-butyldimethylsilyl)oxy-3-(4-methoxybenzyl)oxy-4-methyl-7-(triethylsilyloxy)nonyl]-1,3-dithian-2-yl}butan-1-ol 
• 389085-93-2 (3S,7S)-9-benzyloxy-3-(4-methoxybenzyl)oxy-7-(triethylsilyl)oxy-1-{2-[4-(triethylsilyl)oxybutyl]-1,3-dithian-2-yl}nonan-4-one 

Downstream Products

• 389086-00-4 1-[(2S,6S,8S,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone 
• 389085-99-8 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone 
• 389086-28-6 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-hydroxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone 
• 389086-27-5 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-hydroxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol 
• 389086-26-4 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol 

Relevant academic research and scientific papers

Studies directed toward the total synthesis of pinnatoxin A: Synthesis of the 6,5,6-dispiroketal (BCD ring) system by double hemiketal formation/hetero-Michael addition strategy

An efficient, highly stereoselective synthesis of the C10-C26 portion of pinnatoxin A has been achieved, wherein the key step is a highly stereoselective construction of the 6,5,6-dispiroketal (BCD ring) system by an intramolecular hetero-Michael addition of a hemiketal alkoxide reversibly formed under the influence of lithium methoxide.

A Stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A

(matrix presented) An efficient synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A has been achieved. The key step is a highly stereoselective construction of the dispiroketal (BCD ring) system employing an intramolecular hetero-Michael reaction of a reversibly formed hemiketal alkoxide through the use of LiOMe.