911237-03-1

Upstream product

• 556-56-9 allyl iodid 

Downstream Products

• 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 
• 911237-15-5 [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester 
• 911237-16-6 [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-oxo-non-8-enyl]-phosphonic acid dimethyl ester 
• 911236-84-5 {(S)-4-[(Z)-(2R,3S,8R,9S)-8-Benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-2-oxo-pentyl}-phosphonic acid dimethyl ester 
• 911236-82-3 C₄₁H₆₈O₅Si₂ 
• 911237-09-7 (S)-4-((R)-4-Isopropyl-2-oxo-oxazolidin-3-yl)-3-[(1R,2S)-2-(4-methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-4-oxo-butyronitrile 
• 911237-12-2 (2S,3R,4S)-3-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hept-6-en-1-ol 
• 911237-13-3 ((S)-1-{(1R,2R)-1-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-3-iodo-2-methyl-propyl}-but-3-enyloxy)-tert-butyl-dimethyl-silane 

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