Total synthesis of (±)-crinine via the regioselective stille coupling and Diels-Alder reaction of 3,5-dibromo-2-pyrone

被引:54
作者
Tam, Nguyen Thanh [1 ]
Cho, Cheon-Gyu [1 ]
机构
[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
关键词
D O I
10.1021/ol702907u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective synthesis and Diels-Alder cycloaddition of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone provided a new synthetic route to crinine. The vinyl bromide group can be used as a handle for further derivatization.
引用
收藏
页码:601 / 603
页数:3
相关论文
共 24 条
[1]   Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone: A new ambident diene [J].
Cho, CG ;
Kim, YW ;
Lim, YK ;
Park, JS ;
Lee, H ;
Koo, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :290-293
[2]   Tandem Diels-Alder cycloadditions of 2-pyrone-5-acrylates for the efficient synthesis of novel tetracyclolactones [J].
Chung, Soo-Im ;
Seo, Joobeom ;
Cho, Cheon-Gyu .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6701-6704
[3]   SCELETIUM ALKALOIDS .5. INCORPORATION OF PHENYLALANINE AND EXAMINATION OF NORBELLADINES AS PRECURSORS OF MESEMBRINE ALKALOIDS [J].
JEFFS, PW ;
CAMPBELL, HF ;
FARRIER, DS ;
GANGULI, G ;
MARTIN, NH ;
MOLINA, G .
PHYTOCHEMISTRY, 1974, 13 (06) :933-945
[4]  
Kim HY, 2007, PROG HET CH, V18, P1
[5]   Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives [J].
Kim, WS ;
Lee, JH ;
Kang, J ;
Cho, CG .
TETRAHEDRON LETTERS, 2004, 45 (08) :1683-1687
[6]   Regioselectivity in the Stille coupling reactions of 3,5-dibromo-2-pyrone [J].
Kim, WS ;
Kim, HJ ;
Cho, CG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14288-14289
[7]   Desymmetrization of cyclohexa-2,5-dienes through a diastereoselective protonation-hydroamination cascade [J].
Lebeuf, Raphael ;
Robert, Frederic ;
Schenk, Kurt ;
Landais, Yannick .
ORGANIC LETTERS, 2006, 8 (21) :4755-4758
[8]   TOTAL SYNTHESES OF (+/-)-CRININE AND (+/-)-BUPHANISINE [J].
MARTIN, SF ;
CAMPBELL, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3184-3190
[9]   Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids [J].
McNulty, James ;
Nair, Jerald J. ;
Codina, Carles ;
Bastida, Jaume ;
Pandey, Siyaram ;
Gerasimoff, Jenny ;
Griffin, Carly .
PHYTOCHEMISTRY, 2007, 68 (07) :1068-1074
[10]   SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .5. A STEREOSELECTIVE SYNTHESIS OF CIS-3A-ARYLOCTAHYDROINDOLES AND A NEW SHORT ENTRY TO AMARYLLIDACEAE ALKALOIDS [J].
OVERMAN, LE ;
MENDELSON, LT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5579-5581