Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis

被引:80
作者
Ramachandran, PV [1 ]
Chandra, JS [1 ]
Reddy, MVR [1 ]
机构
[1] Purdue Univ, Herbert C Brown Ctr Borane Res, Dept Chem, W Lafayette, IN 47907 USA
关键词
D O I
10.1021/jo0259358
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.
引用
收藏
页码:7547 / 7550
页数:4
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共 86 条
[41]   Total synthesis of a potent immunosuppressant pironetin [J].
Gurjar, MK ;
Henri, JT ;
Bose, DS ;
Rao, AVR .
TETRAHEDRON LETTERS, 1996, 37 (36) :6615-6618
[42]   ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].
HAFNER, A ;
DUTHALER, RO ;
MARTI, R ;
RIHS, G ;
ROTHESTREIT, P ;
SCHWARZENBACH, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336
[43]   Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions [J].
Harris, JM ;
Keränen, MD ;
Nguyen, H ;
Young, VG ;
O'Doherty, GA .
CARBOHYDRATE RESEARCH, 2000, 328 (01) :17-36
[44]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI DOI 10.1002/0471264180.OR042.02
[45]   Progress in the Mitsunobu reaction. A review [J].
Hughes, DL .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) :127-164
[46]   GONIOTHALAMIN AND ITS DISTRIBUTION IN 4 GONIOTHALAMUS SPECIES [J].
JEWERS, K ;
BLUNDEN, G ;
WETCHAPINAN, S ;
DOUGAN, J ;
MANCHANDA, AH ;
DAVIS, JB ;
KYI, A .
PHYTOCHEMISTRY, 1972, 11 (06) :2025-+
[47]   Total synthesis of the immunosupressant (-)-pironetin (PA48153C) [J].
Keck, GE ;
Knutson, CE ;
Wiles, SA .
ORGANIC LETTERS, 2001, 3 (05) :707-710
[48]   Stereoselectivity of macrocyclic ring-closing olefin metathesis [J].
Lee, CW ;
Grubbs, RH .
ORGANIC LETTERS, 2000, 2 (14) :2145-2147
[49]   Synthesis and antitumor activity of goniofufurone analogues [J].
Mereyala, HB ;
Gadikota, RR ;
Joe, M ;
Arora, SK ;
Dastidar, SG ;
Agarwal, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (09) :2095-2103
[50]   Four new styryllactones from Goniothalamus leiocarpus [J].
Mu, Q ;
Tang, WD ;
Li, CM ;
Lu, Y ;
Sun, HD ;
Zheng, HL ;
Hao, XJ ;
Zheng, QT ;
Wu, N ;
Lou, LG ;
Xu, B .
HETEROCYCLES, 1999, 51 (12) :2969-2976