Total synthesis of nothapodytine B and (±)-mappicine

被引:32
作者
Chavan, SP [1 ]
Sivappa, R [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India
关键词
total synthesis; nothapodytine B; mappicine; Johnson orthoester rearrangement; pyridon;
D O I
10.1016/j.tetlet.2004.03.089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, efficient total synthesis of the naturally occurring antiviral nothapodytine B (2, mappicine ketone) is reported. The approach is based on the successful implementation of the Johnson orthoester rearrangement of allylic alcohol 7 for assembly of a pyridone D ring precursor with the necessary functionalities. Nothapodytine B is converted into mappicine 3 by NaBH4 reduction. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3941 / 3943
页数:3
相关论文
共 42 条
[1]   Total synthesis of nothapodytine B and (-)-mappicine [J].
Boger, DL ;
Hong, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) :1218-1222
[2]   2-pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B [J].
Carles, L ;
Narkunan, K ;
Penlou, S ;
Rousset, L ;
Bouchu, D ;
Ciufolini, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4304-4308
[3]  
Chavan SP, 1999, TETRAHEDRON LETT, V40, P3817
[4]   A 6-STEP SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
COMINS, DL ;
HONG, H ;
SAHA, JK ;
GAO, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5120-5121
[5]   Concise synthesis of mappicine ketone and (+/-)-mappicine [J].
Comins, DL ;
Saha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9623-9624
[6]  
Curran DP, 1995, ANGEW CHEM INT EDIT, V34, P2683
[7]   NEW 4+1 RADICAL ANNULATIONS - A FORMAL TOTAL SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
CURRAN, DP ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5863-5864
[8]  
Das B, 2000, J CHEM RES-S, P476
[9]   The first conversion of camptothecin to (S)-mappicine by an efficient chemoenzymatic method [J].
Das, B ;
Madhusudhan, P ;
Kashinatham, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (11) :1403-1406
[10]   Two efficient methods for the conversion of camptothecin to mappicine ketone, an antiviral lead compound [J].
Das, B ;
Madhusudhan, P ;
Kashinatham, A .
TETRAHEDRON LETTERS, 1998, 39 (5-6) :431-432