CONCISE SYNTHESIS OF YINGZHAOSU-C AND EPI-YINGZHAOSU-C BY PEROXYL RADICAL CYCLIZATION - ASSIGNMENT OF RELATIVE CONFIGURATION

被引：49

作者：

BOUKOUVALAS, J

POULIOT, R

FRECHETTE, Y

机构：

[1] Département de Chimie, Université Laval

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/0040-4039(95)00714-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The antimalarial peroxide yingzhaosu C and its diastereoisomer (epi-yingzhaosu C) have been synthesized by means of tandem peroxyl radical cyclization-oxygen entrapment. The relative configuration of yingzhaosu C is assigned as cis (3) on account of NMR data for both diastereoisomers, (2) and (3), and their precursors (8) and (9).

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页码：4167 / 4170

页数：4

相关论文

共 24 条

[1] ON THE CONVERSION OF DIHYDROARTEMISINIC ACID INTO ARTEMISININ [J].

ACTON, N ;

ROTH, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3610-3614

[2] PERESTERS .5. DI-TERT-BUTYLPEROXYOXALATE [J].

BARTLETT, PD ;

BENZING, EP ;

PINCOCK, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) :1762-1768

[3] 1,2-DIOXOLANE VERSUS 1,2-DIOXANE FORMATION IN THE CYCLIZATION OF AN ALPHA,OMEGA-DIENE HYDROPEROXIDE UNDER POLAR AND FREE-RADICAL CONDITIONS [J].

BLOODWORTH, AJ ;

CURTIS, RJ ;

MISTRY, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :954-955

[4] 2 NEW NORSESTERTERPENE CYCLIC PEROXIDES FROM A MARINE SPONGE, MYCALE (CARMIA) CF SPONGIOSA [J].

CAPON, RJ .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (01) :190-195

[5] TRUNCULIN-A AND TRUNCULIN-B, NORSESTERTERPENE CYCLIC PEROXIDES FROM A MARINE SPONGE, LATRUNCULIA-BREVIS [J].

CAPON, RJ ;

MACLEOD, JK ;

WILLIS, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :339-342

[6] STRUCTURAL AND STEREOCHEMICAL STUDIES ON MARINE NORTERPENE CYCLIC PEROXIDES [J].

CAPON, RJ ;

MACLEOD, JK .

TETRAHEDRON, 1985, 41 (16) :3391-3404

[7] CONFORMATIONAL DEPENDENCE OF C-13 SCS IN 1-METHYL-1-PHENYLCYCLOHEXANES [J].

COOK, MJ ;

NASRI, KA .

MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (07) :644-647

[8] CONVERSION OF ARACHIDONIC-ACID TO THE PROSTAGLANDIN ENDOPEROXIDE PGG(2), A CHEMICAL ANALOG OF THE BIOSYNTHETIC-PATHWAY [J].

COREY, EJ ;

WANG, Z .

TETRAHEDRON LETTERS, 1994, 35 (04) :539-542

[9] INITIATED, TERT-BUTYL HYDROPEROXIDE-LOADED, LOW-TEMPERATURE AUTOXIDATION OF ALKENES - A CHEMOSELECTIVE SYNTHESIS OF ALLYLIC HYDROPEROXIDES, ALLOWING ANALYSIS OF THE REGIOSELECTIVITY OF HYDROGEN-ATOM ABSTRACTION FROM SOME UNSYMMETRICALLY SUBSTITUTED SUBSTRATES [J].

COURTNEIDGE, JL ;

BUSH, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (12) :1531-1538

[10] CARBON CARBON BOND SCISSION DURING THE REACTIONS OF ALLYLIC HYDROPEROXIDES WITH SOME TRANSITION-METAL COMPOUNDS - RESULTS RELEVANT TO A RECENT PROPOSAL [J].

COURTNEIDGE, JL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :381-383