TY - JOUR
T1 - Total synthesis of (-)-Acetylaranotin
AU - Fujiwara, Hideto
AU - Kurogi, Taichi
AU - Okaya, Shun
AU - Okano, Kentaro
AU - Tokuyama, Hidetoshi
PY - 2012/12/21
Y1 - 2012/12/21
N2 - Epidithiodiketopiperazines are an important class of natural products because of their unique structural and biological properties. Among them, acetylaranotin (1), SCH64874 (2), compound 3, emethallicin A (4), MPC1001 (5), and emestrin (6) feature a dihydrooxepine moiety fused to a pyrrolidine/ epidithiodiketopiperazine (Figure 1). They also display a range of intriguing biological activities, such as: inhibitory activity against viral RNA polymerase, antagonistic activity of epidermal growth factor receptor, potent antituberculous activity, inhibitory activity against histamine release, antiproliferative activity against DU145 human prostate cancer cell line, and antagonistic activity of chemokine receptor (CCR2). While numerous synthetic approaches were investigated, only a limited number of successful preparations of the characteristic dihydrooxepine ring have been reported. During the synthetic studies on MPC1001, Peng and Clive established a synthetic method for a pyrrolidinone-fused dihydrooxepine through tetrahydrooxepine formation followed by selenoxide elimination.
AB - Epidithiodiketopiperazines are an important class of natural products because of their unique structural and biological properties. Among them, acetylaranotin (1), SCH64874 (2), compound 3, emethallicin A (4), MPC1001 (5), and emestrin (6) feature a dihydrooxepine moiety fused to a pyrrolidine/ epidithiodiketopiperazine (Figure 1). They also display a range of intriguing biological activities, such as: inhibitory activity against viral RNA polymerase, antagonistic activity of epidermal growth factor receptor, potent antituberculous activity, inhibitory activity against histamine release, antiproliferative activity against DU145 human prostate cancer cell line, and antagonistic activity of chemokine receptor (CCR2). While numerous synthetic approaches were investigated, only a limited number of successful preparations of the characteristic dihydrooxepine ring have been reported. During the synthetic studies on MPC1001, Peng and Clive established a synthetic method for a pyrrolidinone-fused dihydrooxepine through tetrahydrooxepine formation followed by selenoxide elimination.
KW - Aranotin
KW - Diketopiperazine
KW - Oxidation
KW - Rearrangement
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=84871941923&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84871941923&partnerID=8YFLogxK
U2 - 10.1002/anie.201207307
DO - 10.1002/anie.201207307
M3 - Article
C2 - 23161829
AN - SCOPUS:84871941923
VL - 51
SP - 13062
EP - 13065
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 52
ER -