HYDROGEN-ATOM ABSTRACTION REACTIONS IN ORGANIC-SYNTHESIS - A FORMAL TOTAL SYNTHESIS OF RACEMIC PODOPHYLLOTOXIN

被引：37

作者：

KRAUS, GA

WU, YS

机构：

[1] Department of Chemistry, Iowa State University, Ames

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 10期

关键词：

D O I：

10.1021/jo00036a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The key step in a synthesis of 1 was a tandem photoenolization/Diels-Alder reaction to produce 11. Hydrolysis of the acetal and ester followed by oxidation afforded 15, an advanced intermediate in the Meyers synthesis of 1.

引用

页码：2922 / 2925

页数：4

共 25 条

[1] ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN
ANDREWS, RC
TEAGUE, SJ
MEYERS, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7854 - 7858
[2] PHOTOCHEMICAL REACTIONS .2. CYCLOADDITION REACTIONS WITH PHOTOENOLS FROM 2-METHYLBENZALDEHYDE AND RELATED SYSTEMS
ARNOLD, BJ
MELLOWS, SM
SAMMES, PG
WALLACE, TW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (03): : 401 - 409
[3] ASYMMETRIC-SYNTHESIS OF PODOPHYLLOTOXIN ANALOGS
CHARLTON, JL
PLOURDE, GL
KOH, K
SECCO, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (11): : 2022 - 2027
[4] A PHOTOCHEMICALLY-BASED STEREOSELECTIVE ENTRY TO SOME PHENOLIC TRANS 2-ARYLBENZOCYCLOBUTENOL METHYL ETHERS
COLL, G
COSTA, A
DEYA, PM
SAA, JM
[J]. TETRAHEDRON LETTERS, 1991, 32 (02) : 263 - 266
[5] DIRECTING EFFECTS IN HOMOGENEOUS HYDROGENATION WITH [IR(COD)(PCY3)(PY)]PF6
CRABTREE, RH
DAVIS, MW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) : 2655 - 2661
[6] Doyle T. W., 1984, ETOPOSIDE VP 16 CURR
[7] SYNTHESIS OF PODOPHYLLOTOXIN
GENSLER, WJ
GATSONIS, CD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4004 - &
[8] SYNTHESIS OF (+/-)-EPIISOPODOPHYLLOTOXIN
GLINSKI, MB
DURST, T
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (03): : 573 - 575
[9] SYNTHESIS OF PODOPHYLLUM LIGNANS VIA AN ISOLABLE ORTHO-QUINONOID PYRONE
JONES, DW
THOMPSON, AM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (23) : 1797 - 1798
[10] STEREOSELECTIVE SYNTHESIS OF AN ANALOG OF PODOPHYLLOTOXIN BY AN INTRAMOLECULAR DIELS-ALDER REACTION
JUNG, ME
LAM, PY
MANSURI, MM
SPELTZ, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) : 1087 - 1105

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