trans-C-glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one -: Synthesis of the C3-C13 segment of the phorboxazoles A and B

被引:57
作者
Wolbers, P [1 ]
Hoffmann, HMR [1 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
关键词
D O I
10.1016/S0040-4020(98)01196-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1905 / 1914
页数:10
相关论文
共 37 条
[1]   Convergent synthesis of the C31-C46 domain of the phorboxazole natural products [J].
Ahmed, F ;
Forsyth, CJ .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :183-186
[2]  
BERTOZZI C, 1996, MODERN METHODS CARBO, P319
[3]   ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION [J].
BROWN, HC ;
RACHERLA, US ;
PELLECHIA, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1868-1874
[4]   Stereoselective synthesis of the C3-C17 bis-oxane domain of phorboxazole A [J].
Cink, RD ;
Forsyth, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5672-5673
[5]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[6]   8-Oxabicyclo[3.2.1]oct-6-en-3-one as a module for the synthesis of beta-alkoxy-delta-valerolactones relevant to natural products and drugs [J].
Dunkel, R ;
Mentzel, M ;
Hoffmann, HMR .
TETRAHEDRON, 1997, 53 (44) :14929-14936
[7]   Total synthesis of phorboxazole A [J].
Forsyth, CJ ;
Ahmed, F ;
Cink, RD ;
Lee, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5597-5598
[8]   STEREOSELECTIVE SYNTHESIS OF 3-(D-GLYCOPYRANOSYL)PROPENES BY USE OF ALLYLSILANES [J].
HOSOMI, A ;
SAKATA, Y ;
SAKURAI, H .
CARBOHYDRATE RESEARCH, 1987, 171 :223-232
[9]   CHEMISTRY OF ORGANO-SILICON COMPOUNDS .194. HIGHLY STEREOSELECTIVE C-ALLYLATION OF GLYCOPYRANOSIDES WITH ALLYLSILANES CATALYZED BY SILYL TRIFLATE OR IODOSILANE [J].
HOSOMI, A ;
SAKATA, Y ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1984, 25 (22) :2383-2386
[10]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].
IRELAND, RE ;
LIU, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899