title: Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.
abstract: 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.
authors: Univeristy of North Carolina at Chapel Hill, Department of Chemistry, Chapel Hill, NC 27599-3290, USA. crimmins@email.unc.edu
authors: Michael T
authors: MT
authors: Crimmins
authors: J Michael
authors: JM
authors: Ellis
authors: Kyle A
authors: KA
authors: Emmitte
authors: Pamela A
authors: PA
authors: Haile
authors: Patrick J
authors: PJ
authors: McDougall
authors: Jonathan D
authors: JD
authors: Parrish
authors: J Lucas
authors: JL
authors: Zuccarello
mesh_terms: D000478:Alkylation; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000095702:Polyether Toxins
chemical_list: D004987:Ethers; D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins