Synthetic studies on CP-225,917 and CP-263,114: concise synthesis of the bicyclic core using an intramolecular Mukaiyama aldol reaction

被引：19

作者：

Armstrong, A ^{[3
]}

Critchley, TJ

Gourdel-Martin, ME

Kelsey, RD

Mortlock, AA

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] AstraZeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 11期

关键词：

D O I：

10.1039/b202752f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of the bicyclo[4.3.1]dec-1(9)-en-10-one core of the natural products CP-225,917 and CP-263,114 is reported, employing an intramolecular Mukaiyama aldol cyclisation as a key step.

引用

页码：1344 / 1350

页数：7

共 42 条

[1] ALEXAKIS A, 1978, TETRAHEDRON LETT, P4205
[2] Armstrong A, 1998, SYNLETT, P552
[3] Studies towards the biomimetic synthesis of the nonadrides CP-225,917 and CP-263,114
Baldwin, JE
Adlington, RM
Roussi, F
Bulger, PG
Marquez, R
Mayweg, AVW
[J]. TETRAHEDRON, 2001, 57 (34) : 7409 - 7416
[4] Banwell MG, 2001, J CHEM SOC PERK T 1, P2194, DOI 10.1039/b105376k
[5] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS
BURGESS, EM
PENTON, HR
TAYLOR, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 26 - 31
[6] 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
[7] Synthesis of the racemic tetracyclic core of CP-225,917 - a model compound lacking the sidearms of the natural product
Clive, DLJ
Sun, SY
[J]. TETRAHEDRON LETTERS, 2001, 42 (36) : 6267 - 6270
[8] SYNTHESIS OF 1,2,3,4-TETRAHYDRO-7-HYDROXY-4-ISOPROPYL-1,6-DIMETHYLNAPHTHALENE . A DEGRADATION PRODUCT OF COPAENE
COCKER, W
SAINSBUR.DM
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAY): : 3319 - &
[9] SILICON-MEDIATED ANNULATION .1. A SYNTHESIS OF TETRAHYDROPYRAN-4-ONES, OXEPAN-4-ONES, AND OXOCAN-4-ONES VIA INTRAMOLECULAR DIRECTED ALDOL REACTIONS
COCKERILL, GS
KOCIENSKI, P
TREADGOLD, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10): : 2093 - 2100
[10] The introduction of substituted vinyl groups IV (Primary 1-alkenyl) alkyl malonic esters
Cope, AC
Hartung, WH
Hancock, EM
Crossley, FS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 314 - 316

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