A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes

被引:46
作者
Bacqué, E
Pautrat, F
Zard, SZ [1 ]
机构
[1] Ecole Polytech, CNRS, Organ Synth Lab, F-91128 Palaiseau, France
[2] AVENTIS Pharma, F-93235 Romainville, France
关键词
D O I
10.1021/ol027312m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short synthesis of the tricyclic skeleton of pleuromutilin is reported, featuring an unusually efficient 8-endo-trig radical cyclization of a xanthate precursor. In the course of this study, a one-carbon ring expansion leading to cycloheptenes was uncovered.
引用
收藏
页码:325 / 328
页数:4
相关论文
共 16 条
[1]   A flexible strategy for the divergent modification of pleuromutilin [J].
Bacqué, E ;
Pautrat, F ;
Zard, SZ .
CHEMICAL COMMUNICATIONS, 2002, (20) :2312-2313
[2]   MULTIPLE RADICAL ADDITIONS - AN EXPEDIENT ENTRY INTO COMPLEX FRAMEWORKS [J].
BARTON, DHR ;
DASILVA, E ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :285-287
[3]   FORMATION OF SOME BICYCLIC AND TRICYCLIC SYSTEMS BY RADICAL RING-CLOSURE [J].
BECKWITH, ALJ ;
ROBERTS, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5893-5901
[4]   SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .2. A STEREOCONTROLLED ASSEMBLY OF (+/-)-PLEUROMUTILIN VIA A REMARKABLE STERICALLY DEMANDING OXY-COPE REARRANGEMENT [J].
BOECKMAN, RK ;
SPRINGER, DM ;
ALESSI, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8284-8286
[5]   Chemistry of acyl radicals [J].
Chatgilialoglu, C ;
Crich, D ;
Komatsu, M ;
Ryu, I .
CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069
[6]   FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].
DOWD, P ;
ZHANG, W .
CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115
[7]   TOTAL SYNTHESIS OF (+/-)-PLEUROMUTILIN [J].
GIBBONS, EG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1767-1769
[8]   Pleuromutilin antibiotics [J].
Hunt, E .
DRUGS OF THE FUTURE, 2000, 25 (11) :1163-1168
[9]   ANIONIC OXY-COPE REACTION OF A DIVINYL CYCLOBUTANOL, PLEUROMUTILIN MODEL STUDY [J].
KAHN, M .
TETRAHEDRON LETTERS, 1980, 21 (47) :4547-4548
[10]   (+)-PLEUROMUTILIN SYNTHETIC STUDIES - EXAMPLES OF INTRAMOLECULAR HYDROGEN ABSTRACTION BY THE BETA-CARBON OF A 2-CYCLOPENTENONE SUBUNIT WITH RESULTANT ALPHA-COUPLING [J].
PAQUETTE, LA ;
PANSEGRAU, PD ;
WIEDEMAN, PE ;
SPRINGER, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1461-1466