874660-19-2

Upstream product

• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 
• 874660-40-9 (R)-2-(4-Methoxy-benzyloxy)-pent-4-enal 
• 874660-17-0 3-hydroxy-4-(4-methoxy-benzyloxy)-hept-6-enoic acid tert-butyl ester 
• 874660-41-0 (R)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,3-diol 
• 13154-24-0 triisopropylsilyl chloride 

Downstream Products

• 874660-42-1 (R)-4-(4-Methoxy-benzyloxy)-1-triisopropylsilanyloxy-hept-6-en-3-one 
• 874660-44-3 (S)-3-{(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionyl}-4-isopropyl-oxazolidin-2-one 
• 874660-46-5 (R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol 
• 874660-21-6 (S)-4-Isopropyl-3-{2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetyl}-oxazolidin-2-one 

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.

Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A

(Chemical Equation Presented) A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.