An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin

被引:39
作者
Cook, Silas P.
Danishefsky, Samuel J.
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem, New York, NY 10021 USA
关键词
D O I
10.1021/ol062067i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hypervalent iodine-mediated oxidative dearomatization/Diels-Alder cascade was examined in the context of the natural product 11-O-debenzoyltashironin. Interestingly, the regioselectivity of the Diels-Alder reaction can be completely switched by changing the dienophile. Trapping of allyl alcohols during the oxidative dearomatization gives rise to the five-membered acetal, while trapping of allenyl alcohols results in the six-membered acetal.
引用
收藏
页码:5693 / 5695
页数:3
相关论文
共 7 条
[1]   TASHIRONIN, A PLAUSIBLE BIOSYNTHETIC PRECURSOR OF ANISATIN-TYPE SESQUITERPENES [J].
FUKUYAMA, Y ;
SHIDA, N ;
KODAMA, M .
TETRAHEDRON LETTERS, 1995, 36 (04) :583-586
[2]   Structure and neurotrophic activity of seco-prezizaane-type sesquiterpenes from Illicium merrillianum [J].
Huang, JM ;
Yokoyama, R ;
Yang, CS ;
Fukuyama, Y .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (04) :428-431
[3]   INDIUM-MEDIATED COUPLING OF ALDEHYDES WITH PROP-2-YNYL BROMIDES IN AQUEOUS-MEDIA [J].
ISAAC, MB ;
CHAN, TH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1003-1004
[4]   Masked o-benzoquinones in organic synthesis [J].
Liao, CC ;
Peddinti, RK .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :856-866
[5]   PHENOLIC OXIDATION WITH (DIACETOXYIODO)BENZENE [J].
PELTER, A ;
ELGENDY, S .
TETRAHEDRON LETTERS, 1988, 29 (06) :677-680
[6]   HYPERVALENT IODINE OXIDATION OF PARA-ALKOXYPHENOLS AND RELATED-COMPOUNDS - A GENERAL-ROUTE TO PARA-BENZOQUINONE MONOACETALS AND SPIRO LACTONES [J].
TAMURA, Y ;
YAKURA, T ;
HARUTA, J ;
KITA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3927-3930
[7]   Applications of total synthesis to problems in neurodegeneration: Fascinating chemistry along the way [J].
Wilson, Rebecca M. ;
Danishefsky, Samuel J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (08) :539-549