TY - JOUR
T1 - Total synthesis of (±)-xanthocidin using FeCl3-mediated Nazarov reaction
AU - Yaji, Kentaro
AU - Shindo, Mitsuru
N1 - Funding Information:
This research was partially supported by a Grant-in-Aid for Scientific Research (B) ( 22390002 ) and the Program for the Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN). One of the authors (K.Y.) also acknowledges the support of the JSPS.
PY - 2010/12/24
Y1 - 2010/12/24
N2 - The total synthesis of the antibiotic, (±)-xanthocidin (1), is described. The FeCl3-promoted fast Nazarov reaction of the β-alkoxy divinyl ketone in the presence of t-BuOH provided the α-exo-methylene cyclopentenone, which is the core skeleton of this natural product. After methoxymethyl (MOM) esterification and protection of the reactive exo-methylene unit with a phenylseleno group, dihydroxylation, followed by oxidation, gave xanthocidin MOM ester. Finally, this ester was converted into (±)-xanthocidin (1) under mild conditions.
AB - The total synthesis of the antibiotic, (±)-xanthocidin (1), is described. The FeCl3-promoted fast Nazarov reaction of the β-alkoxy divinyl ketone in the presence of t-BuOH provided the α-exo-methylene cyclopentenone, which is the core skeleton of this natural product. After methoxymethyl (MOM) esterification and protection of the reactive exo-methylene unit with a phenylseleno group, dihydroxylation, followed by oxidation, gave xanthocidin MOM ester. Finally, this ester was converted into (±)-xanthocidin (1) under mild conditions.
UR - http://www.scopus.com/inward/record.url?scp=78649683693&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78649683693&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.10.084
DO - 10.1016/j.tet.2010.10.084
M3 - Article
AN - SCOPUS:78649683693
SN - 0040-4020
VL - 66
SP - 9808
EP - 9813
JO - Tetrahedron
JF - Tetrahedron
IS - 52
ER -