TY - JOUR
T1 - Enantioselective total synthesis of brevetoxin A
T2 - Unified strategy for the B, E, G, and J subunits
AU - Crimmins, Michael T.
AU - Ellis, J. Michael
AU - Emmitte, Kyle A.
AU - Haile, Pamela A.
AU - McDougall, Patrick J.
AU - Parrish, Jonathan D.
AU - Zuccarello, J. Lucas
PY - 2009/9/14
Y1 - 2009/9/14
N2 - 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.
AB - 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.
KW - Asymmetric synthesis
KW - Chiral auxiliaries
KW - Glycolate alkylation
KW - Ring-closing metathesis
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=70349100870&partnerID=8YFLogxK
U2 - 10.1002/chem.200900776
DO - 10.1002/chem.200900776
M3 - Article
C2 - 19650091
AN - SCOPUS:70349100870
SN - 0947-6539
VL - 15
SP - 9223
EP - 9234
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 36
ER -