911236-73-2

Upstream product

• 95530-58-8 (R)-4-isopropyloxazolidin-2-one 
• 911236-96-9 [(1R,2S)-2-(4-Methoxy-benzyloxy)-4-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid 
• 911236-71-0 (S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-one 
• 911236-95-8 (S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol 
• 911236-72-1 (3R,4S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol 
• 911236-93-6 (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one 
• 911236-70-9 (S)-4-(4-Methoxy-benzyloxy)-6-methyl-3-oxo-hept-6-enoic acid ethyl ester 
• 911236-94-7 (S)-4-(4-Methoxy-benzyloxy)-6-methyl-hept-6-ene-1,3-diol 

Downstream Products

• 911236-97-0 (R)-3-{(S)-3-Benzyloxy-2-[(1R,2S)-2-(4-methoxy-benzyloxy)-4-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionyl}-4-isopropyl-oxazolidin-2-one 
• 911236-88-9 2-{2-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-propyl}-7-(4-methoxy-benzyloxy)-9,10a-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-1,5-dioxa-benzocycloocten-3-one 
• 911236-87-8 2-{2-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-propyl}-7-(4-methoxy-benzyloxy)-9,10a-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-1,5-dioxa-benzocycloocten-3-one 
• 911236-85-6 5-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-[3-hydroxy-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-2-yl]-hex-1-en-3-one 
• 911236-86-7 C₆₄H₁₀₀O₉Si₂ 
• 911236-89-0 C₅₀H₆₈O₁₀ 
• 911236-90-3 C₄₂H₆₀O₉ 
• 911236-91-4 C₄₁H₅₈O₈ 
• 911237-02-0 (2S,3R,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-3-ol 
• 911237-01-9 (2S,3R,5S,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-3-ol 
• 911236-74-3 (R)-3-Benzyloxy-2-[(1R,2S)-2-(4-methoxy-benzyloxy)-4-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propan-1-ol 
• 911236-77-6 (2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-3-one 
• 911236-98-1 (S)-3-Benzyloxy-2-[(1R,2S)-2-(4-methoxy-benzyloxy)-4-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde 
• 911237-17-7 (2S,3R,5R,7S,8R)-2-Hydroxymethyl-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-3-ol 

Relevant academic research and scientific papers

Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits

Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.

Improved synthesis of the ABCDE fragment of brevetoxin A

A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits