Studies towards the taxane ring system via a cascade macrocyclisation-transannulation strategy

被引:6
作者
Houldsworth, SJ [1 ]
Pattenden, G [1 ]
Pryde, DC [1 ]
Thomson, NM [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 08期
关键词
D O I
10.1039/a700784a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the omega-iodoacetylene 6 with Bu3SnH-AIBN produces the taxane ring system 9 (45-60%) by way of transannular cyclisation from the macrocyclic vinyl radical intermediate 8, whereas the analogous iodoacetylenes 5a, 11 and 13a, together with the iodopolyenones 12a, 14a and 17, failed to give corresponding taxane systems, i.e. 7, 16 and 19 on similar treatment; instead only products resulting from direct reduction of the carbon-iodine bonds in these substrates were obtained.
引用
收藏
页码:1091 / 1093
页数:3
相关论文
共 35 条
[11]   Total synthesis of baccatin III and taxol [J].
Danishefsky, SJ ;
Masters, JJ ;
Young, WB ;
Link, JT ;
Snyder, LB ;
Magee, TV ;
Jung, DK ;
Isaacs, RCA ;
Bornmann, WG ;
Alaimo, CA ;
Coburn, CA ;
DiGrandi, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :2843-2859
[12]  
DANISHEFSKY SJ, 1995, ANGEW CHEM INT EDIT, V34, P1723
[13]   Total synthesis of (+/-)-taxusin [J].
Hara, R ;
Furukawa, T ;
Horiguchi, Y ;
Kuwajima, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9186-9187
[14]   A TANDEM RADICAL MACROCYCLIZATION - RADICAL TRANSANNULATION STRATEGY TO THE TAXANE RING-SYSTEM [J].
HITCHCOCK, SA ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1992, 33 (33) :4843-4846
[15]   FIRST TOTAL SYNTHESIS OF TAXOL .1. FUNCTIONALIZATION OF THE B-RING [J].
HOLTON, RA ;
SOMOZA, C ;
KIM, HB ;
LIANG, F ;
BIEDIGER, RJ ;
BOATMAN, PD ;
SHINDO, M ;
SMITH, CC ;
KIM, SC ;
NADIZADEH, H ;
SUZUKI, Y ;
TAO, CL ;
VU, P ;
TANG, SH ;
ZHANG, PS ;
MURTHI, KK ;
GENTILE, LN ;
LIU, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1597-1598
[16]  
HOULDSWORTH SJ, 1996, THESIS U NOTTINGHAM
[17]   SYNTHETIC APPLICATIONS OF THE TANDEM ALDOL CONDENSATION-RADICAL CYCLIZATION SEQUENCE - A NEW AND HIGHLY CONVERGENT METHOD FOR THE ANNULATION OF CARBOCYCLES [J].
LEONARD, WR ;
LIVINGHOUSE, T .
TETRAHEDRON LETTERS, 1985, 26 (52) :6431-6434
[18]   A cycloaddition approach to tricyclic taxoid skeletons [J].
Lu, YF ;
Fallis, AG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (12) :2239-2252
[19]   Taxane diterpenes .3. Formation of the eight-membered B-ring by semi-pinacol rearrangement [J].
Magnus, P ;
Diorazio, L ;
Donohoe, TJ ;
Giles, M ;
Pye, P ;
Tarrant, J ;
Thom, S .
TETRAHEDRON, 1996, 52 (45) :14147-14176
[20]   FACILE ACCESS TO THE ABC RING-SYSTEM OF THE TAXANE DITERPENES VIA ANIONIC OXY-COPE REARRANGEMENTS [J].
MARTIN, SF ;
ASSERCQ, JM ;
AUSTIN, RE ;
DANTANARAYANA, AP ;
FISHPAUGH, JR ;
GLUCHOWSKI, C ;
GUINN, DE ;
HARTMANN, M ;
TANAKA, T ;
WAGNER, R ;
WHITE, JB .
TETRAHEDRON, 1995, 51 (12) :3455-3482