SYNTHESIS AND STEREOCHEMISTRY OF DESACETOXYMATRICARIN AND STEREOCHEMISTRY OF MATRICARIN

被引：50

作者：

WHITE, EH

EGUCHI, S

MARX, JN

机构：

[1] Department of Chemistry, The Johns Hopkins University, Baltimore

来源：

TETRAHEDRON | 1969年 / 25卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(01)82761-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Desacetoxymatricarin (IV), a sesquiterpene lactone found in the genus Artemisia and in the form of 8-hydroxy and acetoxy derivatives in the genus Achillea, has been synthesized from α-santonin by a sequence that allows assignment of the full stereochemistry. The stereochemistry of matricarin (V) has also been determined. The unusual stability to dehydration of some of the cyclopentyl-type alcohols, which were intermediates in the synthesis, is discussed. © 1969.

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页码：2099 / +

页数：1

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共 56 条

[1] STUDIES ON ANTHELMINTICS .12. SANTONIN .3. THE TOTAL SYNTHESIS OF SANTONIN [J].

ABE, Y ;

HARUKAWA, T ;

ISHIKAWA, H ;

MIKI, T ;

SUMI, M ;

TOGA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (07) :1422-1426

[2] STUDIES ON ANTHELMINTICS .11. SANTONIN .2. THE SYNTHESIS OF NEW STEROISOMERS OF SANTONIN [J].

ABE, Y ;

HARUKAWA, T ;

ISHIKAWA, H ;

MIKI, T ;

SUMI, M ;

TOGA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (07) :1416-1421

[3] NMR SPECTRA OF CYCLIC AND ACYLIC 2,3-DISUBSTITUTED BUTANES [J].

ANET, FAL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :747-&

[4]

ARCHER JD, 1962, P CHEM SOC, P111

[5] PHOTOCHEMISCHE REAKTIONEN .2. UBER GEGENSEITIGE BEZIEHUNGEN UND UMWANDLUNGEN BEI BESTRAHLUNGSPRODUKTEN DES SANTONINS [J].

ARIGONI, D ;

BOSSHARD, H ;

BRUDERER, H ;

BUCHI, G ;

JEGER, O ;

KREBAUM, LJ .

HELVETICA CHIMICA ACTA, 1957, 40 (06) :1732-1749

[6] TERPENOIDS OF SONCHUS .3. SESQUITERPENE LACTONES OF S JACQUINI DC S PINNATUS AIT AND S RADICATUS AIT [J].

BARRERA, JB ;

FUNES, JLB ;

GONZALEZ, AG .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (14) :1298-&

[7] PHOTOCHEMICAL TRANSFORMATIONS .2. THE CONSTITUTION OF LUMISANTONIN [J].

BARTON, DHR ;

DEMAYO, P ;

SHAFIQ, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (JAN) :140-146

[8] SOME PHOTOCHEMICAL REARRANGEMENTS [J].

BARTON, DHR .

HELVETICA CHIMICA ACTA, 1959, 42 (07) :2604-2616

[9]

BARTON DHR, 1962, P CHEM SOC LONDON, P112

[10] PHOTOCHEMICAL TRANSFORMATIONS .14. SOME ANALOGUES OF ISOPHOTOSANTONIC LACTONE [J].

BARTON, DHR ;

LEVISALLES, JE ;

PINHEY, JT .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (SEP) :3472-&

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