Evaluation of asymmetric Diels-Alder approaches for the synthesis of the cyclohexene subunit of CP-225,917 and CP-263,114

被引：8

作者：

Armstrong, A ^{[1
]}

Davies, NGM ^{[1
]}

Martin, NG ^{[1
]}

Rutherford, AP ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

CP-compounds; Diels-Alder; oxazolidinone; cyclopropanation;

D O I：

10.1016/S0040-4039(03)00835-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of a functionalised cyclohexenone required for total synthesis of CP-225,917 and CP-263,114 is reported, using a Lewis acid-promoted Diels-Alder reaction between a 2-sityloxy-1,3-diene and a dienophile bearing an oxazolidinone auxiliary. A novel method for appendage of the exocyclic malonate unit, via cyclopropane ring opening, is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3915 / 3918

页数：4

共 45 条

[1] Synthetic studies on CP-225,917 and CP-263,114: concise synthesis of the bicyclic core using an intramolecular Mukaiyama aldol reaction
Armstrong, A
Critchley, TJ
Gourdel-Martin, ME
Kelsey, RD
Mortlock, AA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (11): : 1344 - 1350
[2] Approaches to the γ-lactone unit of CP-225,917 and CP-263,114
Armstrong, A
Critchley, TJ
Gourdel-Martin, ME
Kelsey, RD
Mortlock, AA
[J]. TETRAHEDRON LETTERS, 2002, 43 (34) : 6027 - 6030
[3] Armstrong A, 1998, SYNLETT, P552
[4] Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside
Boeckman, RK
Liu, YG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 7984 - 7985
[5] Toward the development of a general chiral auxiliary.: Part 6:: Structural effects on diastereoselection using camphor derived lactams:: evaluation of (1R,4S)-1,7,7-trimethyl-3-azabicyclo[2.2.1]hept-5-en-3-one as a chiral controller
Boeckman, RK
Laci, MA
Johnson, AT
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (02) : 205 - 217
[6] TOWARD THE DEVELOPMENT OF A GENERAL CHIRAL AUXILIARY .1. PREPARATION OF A NEW CLASS OF CAMPHOR LACTAM IMIDES AND THEIR APPLICATION TO THE CONSTRUCTION OF QUATERNARY CENTERS VIA DIELS-ALDER CYCLOADDITION
BOECKMAN, RK
NELSON, SG
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2258 - 2260
[7] Synthesis of (+)-CP-263,114
Chen, C
Layton, ME
Sheehan, SM
Shair, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) : 7424 - 7425
[8] An efficient approach to bridged-bicyclic rings via intramolecular diazo ketone insertion
Chen, L
Zhang, XQ
Schultz, A
[J]. TETRAHEDRON LETTERS, 2002, 43 (26) : 4711 - 4715
[9] Synthesis of the racemic tetracyclic core of CP-225,917: use of a strain-assisted Cope rearrangement
Clive, DLJ
Ou, L
[J]. TETRAHEDRON LETTERS, 2002, 43 (25) : 4559 - 4563
[10] Dabrah TT, 1997, J ANTIBIOT, V50, P1

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