Towards the total synthesis of phorboxazoles A and B:: Stereocontrolled synthesis of a C20-C32 subunit

被引:76
作者
Paterson, I [1 ]
Arnott, EA [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(98)01539-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C-20-C-32 phorboxazole subunit 4, containing 5 stereocentres, was prepared in 8 steps (34%) from ethyl ketone (S)-7. Key steps included a boron-mediated anti aldol reaction and an intramolecular hetero-Michael reaction. Installation of the C-19-C-20 (E)-alkene using a Wittig reaction produced a C-15-C-32 fragment, including both oxazoles present in the natural product. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7185 / 7188
页数:4
相关论文
共 27 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]  
ARNOTT EA, UNPUB
[3]   Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].
Banwell, MG ;
Bui, CT ;
Pham, HTT ;
Simpson, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :967-969
[4]   Stereocontrolled synthesis of cyclic ethers by intramolecular hetero-Michael addition .5. Synthesis of all diastereoisomers of 2,3,5,6-tetrasubstituted tetrahydropyrans [J].
Betancort, JM ;
Martin, VS ;
Padron, JM ;
Palazon, JM ;
Ramirez, MA ;
Soler, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4570-4583
[5]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[6]   SYNTHESIS OF THE LOWER SUBUNIT OF RHIZOXIN [J].
BOGER, DL ;
CURRAN, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2235-2244
[7]   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
[8]  
Cowden C. J., 1997, ORG REACTIONS, V51, P1
[9]   SYNTHETIC STUDIES ON HALICHONDRINS - A NEW PRACTICAL SYNTHESIS OF THE C.1-C.12 SEGMENT [J].
DUAN, JJW ;
KISHI, Y .
TETRAHEDRON LETTERS, 1993, 34 (47) :7541-7544
[10]   SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6447-6449