365212-80-2

Upstream product

• 365212-77-7 (S)-2-(3-Benzyloxy-propyl)-5-methyl-2,3-dihydro-pyran-4-one 
• 824-94-2 p-methoxybenzyl chloride 
• 72476-03-0 (E)-3-methyl-4-methoxy-2-[(trimethylsilyl)oxy]-1,3-butadiene 
• 5470-84-8 4-benzyloxybutanal 
• 365212-88-0 2-allyl-6-(3-benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-3-ol 
• 365212-78-8 (2S,4R)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-5-methyl-3,4-dihydro-2H-pyran 
• 884004-54-0 (2S,4R)-2-(3-Benzyloxy-propyl)-5-methyl-3,4-dihydro-2H-pyran-4-ol 
• 365212-79-9 Acetic acid (2R,3S,4R,6S)-2-allyl-6-(3-benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-3-yl ester 

Downstream Products

• 884004-80-2 2-allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-(triisopropyl-silanyloxy)-hexahydro-pyrano[3,2-b]pyran-3-one 
• 884004-83-5 C₂₈H₄₄O₅Si 
• 884004-84-6 [2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane 
• 884004-85-7 C₂₆H₄₀O₆Si 
• 884004-86-8 C₂₆H₄₂O₆Si 
• 884004-88-0 3-(triisopropyl-silanyloxy)-propionic acid 2-allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-(triisopropyl-silanyloxy)-octahydro-pyrano[3,2-b]pyran-3-yl ester 
• 884004-89-1 3-(triisopropyl-silanyloxy)-propionic acid 2-allyl-6-(3-benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yl ester 
• 884004-90-4 2-(3-benzyloxy-propyl)-4a,10a-dimethyl-4-(triisopropyl-silanyloxy)-7-[2-(triisopropyl-silanyloxy)-ethyl]-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracene 
• 884004-92-6 7-(3-benzyloxy-propyl)-4a,10a-dimethyl-5-(triisopropyl-silanyloxy)-2-[2-(triisopropyl-silanyloxy)-ethyl]-decahydro-1,8,10-trioxa-anthracen-3-ol 

Relevant academic research and scientific papers

Total synthesis of gambierol: The generation of the A-C and F-H subunits by using a C-glycoside centered strategy

Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3-diaxial orientation to one another. Herein we describe the generation of gambierol's A-C and F-H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether-olefin RCM strategy to fused polycyclic ethers. This work has both enabled us to generate sufficient quantities of the gambierol precursors and has enabled us to better understand the chemical transformations that were key to these efforts. Fundamental work included efforts to C-glycosides and C-ketosides, Claisen rearrangements, and enol ether-olefin RCM reactions.

C-glycosides to fused polycyclic ethers. An efficient entry into the A-D ring system of gambierol.

[reaction: see text]. This Letter describes our use of C-glycosides to synthesize the A-D ring system of the marine ladder toxin gambierol in 20 steps.