Synthetic studies towards phorboxazole A. A convergent synthesis of the C31-C46 polyene oxane-hemiacetal side chain

被引:61
作者
Pattenden, G [1 ]
Plowright, AT [1 ]
Tornos, JA [1 ]
Ye, T [1 ]
机构
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1016/S0040-4039(98)01258-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural product phorboxazole A, which accommodates five asymmetric centres, three carbon-to-carbon double bonds and an oxane-hemiacetal unit, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6099 / 6102
页数:4
相关论文
共 20 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]  
BAUDIN JB, 1993, B SOC CHIM FR, V130, P336
[3]  
BAUDIN JB, 1993, B SOC CHIM FR, V130, P856
[4]  
Bellingham R, 1996, SYNTHESIS-STUTTGART, P285
[5]   VERSATILE ALPHA-PINENE-BASED BORANE REAGENTS FOR ASYMMETRIC SYNTHESES [J].
BROWN, HC ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :1-19
[7]  
Chattopadhyay SK, 1997, SYNLETT, P1342
[8]   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
[9]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[10]   ELABORATION OF ALDEHYDES AND KETONES TO ALKYNES - IMPROVED METHODOLOGY [J].
GILBERT, JC ;
WEERASOORIYA, U .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4997-4998