INTRAMOLECULAR PARTICIPATION REACTIONS IN LABDA-8(17),14-DIEN-13-OL (MANOOL) DERIVATIVES

被引：4

作者：

GRANT, PK

HANTON, LR

TSAI, SF

YAP, TM

机构：

[1] Department of Chemistry, University of Otago

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1991年 / 44卷 / 03期

关键词：

D O I：

10.1071/CH9910433

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis acid treatment of a series of hydroxy epoxides promoted intramolecular nucleophilic epoxide opening to give hydroxy cyclic ethers. The regioselectivity of epoxide opening is controlled by a preference for S(N)2 attack at the more accessible epoxide carbon, provided this does not involve the formation of a strained ether ring. An intramolecular acetate transfer occurs in order to achieve the regioselective opening.

引用

收藏

页码：433 / 446

页数：14

相关论文

共 12 条

[1] A NEW SYNTHESIS OF LACTONES - APPLICATION TO (+-)-MEVALONOLACTONE [J].

FETIZON, M ;

GOLFIER, M ;

LOUIS, JM .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (19) :1118-&

[2] OZONOLYSIS OF DERIVATIVES OF LABDA-8(17),14-DIEN-13-OL (MANOOL) AND THEIR CONVERSION INTO LARGE RING UNSATURATED LACTONES [J].

GRANT, PK ;

CHEE, KL ;

PRASAD, JS ;

THO, MY .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (05) :711-725

[3] DITERPENE CHEMISTRY .4. TRANSFORMATIONS OF 8(17),14-LABDADIEN-13-OL [J].

GRANT, PK ;

WEAVERS, RT .

TETRAHEDRON, 1974, 30 (15) :2385-2395

[4] STRUCTURE ODOR STUDIES WITH SOME DITERPENE DERIVED ACETALS [J].

GRANT, PK ;

ROWAN, DD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (09) :1959-1973

[5]

Ibers J. A., 1974, INT TABLES XRAY CRYS, VIV

[6]

MAIN P, 1977, MULTAN 77

[7] A STEREOSELECTIVE SYNTHESIS OF ALPHA- AND BETA-AGAROFURAN [J].

MARSHALL, JA ;

PIKE, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :435-&

[8] MECHANISMS OF EPOXIDE REACTIONS [J].

PARKER, RE ;

ISAACS, NS .

CHEMICAL REVIEWS, 1959, 59 (04) :737-799

[9] ZUR KENNTNIS DER DITERPENE .65. UBER DIE STRUKTUR UND UMWANDLUNGEN VON ZWEI STEREOISOMEREN RIECHSTOFFEN C18H30O2 AUS MANOOL [J].

SCHEIDEGGER, U ;

SCHAFFNER, K ;

JEGER, O .

HELVETICA CHIMICA ACTA, 1962, 45 (01) :400-+

[10]

SHELDRICK GM, 1976, SHELX PROGRAM CRYSTA