Synthesis of the racemic tetracyclic core of CP-225,917 - a model compound lacking the sidearms of the natural product

被引:18
作者
Clive, DLJ [1 ]
Sun, SY [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Peterson reaction; anhydride; lactone; ruthenium dioxide; bridgehead olefin; quaternary carbon;
D O I
10.1016/S0040-4039(01)01286-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compound 3, representing the tetracyclic core structure of CP-225,917, was prepared from bridgehead olefin 9, which was first converted into ketone 13. Peterson olefination then gave 15, and this was elaborated into the anhydride 19, from which crystalline 3 was reached by a sequence of deprotection and oxidation steps. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6267 / 6270
页数:4
相关论文
共 32 条
[1]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[2]   Stereoconvergent palladium-catalyzed carbonylation of both E and Z isomers of a 2-trifloxy-1,3-butadiene [J].
Bio, MM ;
Leighton, JL .
ORGANIC LETTERS, 2000, 2 (18) :2905-2907
[3]   Synthesis of (+)-CP-263,114 [J].
Chen, C ;
Layton, ME ;
Sheehan, SM ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7424-7425
[4]   An approach to the anhydride unit of CP-225,917 and CP-263,114 [J].
Clive, DLJ ;
Sun, SY ;
Gagliardini, V ;
Sano, MK .
TETRAHEDRON LETTERS, 2000, 41 (33) :6259-6263
[5]   Synthesis of tricyclic bridgehead olefins related to the core structure of CP-225,917 and CP-263,114 - solvent, strain, and substitution effects on siloxy-Cope rearrangements [J].
Clive, DLJ ;
Sun, SY ;
He, X ;
Zhang, JH ;
Gagliardini, V .
TETRAHEDRON LETTERS, 1999, 40 (25) :4605-4609
[6]   ASCIDIATRIENOLIDE-A IS A 10-MEMBERED LACTONE [J].
CONGREVE, MS ;
HOLMES, AB ;
HUGHES, AB ;
LOONEY, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5815-5816
[7]   Total synthesis of dysidiolide [J].
Corey, EJ ;
Roberts, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12425-12431
[8]   Dihydro- and tetrahydrofuran ring-opening reactions directed towards the synthesis of CP-263,114 [J].
Davies, HML ;
Ren, PD .
TETRAHEDRON LETTERS, 2000, 41 (47) :9021-9024
[9]   An exploratory study of type II [3+4] cycloadditions between vinylcarbenoids and dienes [J].
Davies, HML ;
Calvo, RL ;
Townsend, RJ ;
Ren, PD ;
Churchill, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4261-4268
[10]   A TOTAL SYNTHESIS OF AN ANTIBACTERIAL CLERODANE, 16-HYDROXYCLERODA-3,13(14)Z-DIEN-15,16-OLIDE [J].
HAGIWARA, H ;
INOME, K ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07) :757-764