Synthesis of the azaphilones (+)-sclerotiorin and (+)-8- O -methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization

TY - JOUR

T1 - Synthesis of the azaphilones (+)-sclerotiorin and (+)-8- O -methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization

AU - Germain, Andrew R.

AU - Bruggemeyer, Daniel M.

AU - Zhu, Jianglong

AU - Genet, Cedric

AU - O'Brien, Peter

AU - Porco, John A.

PY - 2011/4/15

Y1 - 2011/4/15

N2 - Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-i-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O- methylsclerotiorinamine.

AB - Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-i-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O- methylsclerotiorinamine.

UR - http://www.scopus.com/inward/record.url?scp=79953892780&partnerID=8YFLogxK

U2 - 10.1021/jo102448n

DO - 10.1021/jo102448n

M3 - Article

C2 - 21401026

AN - SCOPUS:79953892780

SN - 0022-3263

VL - 76

SP - 2577

EP - 2584

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -