AN IMPROVED SYNTHESIS OF (-)-DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTHO[2,1-B]FURAN VIA OZONOLYSIS OF (-)-SCLAREOL

被引：18

作者：

BARTON, DHR

TAYLOR, DK

TSE, C

机构：

[1] Department of Chemistry, Texas A and M University, College Station

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 51期

关键词：

D O I：

10.1016/0040-4039(94)88497-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ozonolysis of (-)-sclareol 1 under a wide range of experimental conditions has been investigated. The addition of one of the following; sodium periodate, sodium iodate, iodine or potassium iodide affords after workup the methyl-ketone 2 in excellent yield. Further elaboration of 2 afforded the title compound 4 h high yield.

引用

收藏

页码：9505 / 9508

页数：4

相关论文

共 10 条

[1]

BAILEYPS, 1978, OZONOLYSIS ORGANIC C, P147

[2] SYNTHESIS OF AMBROX(R) FROM (-)-SCLAREOL AND (+)-CIS-ABIENOL [J].

BARRERO, AF ;

ALVAREZMANZANEDA, EJ ;

ALTAREJOS, J ;

SALIDO, S ;

RAMOS, JM .

TETRAHEDRON, 1993, 49 (45) :10405-10412

[3] AN EFFICIENT SYNTHESIS OF (-)-DODECAHYDRO-3A,6,6,9A-TETRAMETHYLNAPHTHOL[2,1-B]FURAN FROM (-)-SCLAREOL [J].

BARTON, DHR ;

PAREKH, SI ;

TAYLOR, DK ;

TSE, CI .

TETRAHEDRON LETTERS, 1994, 35 (32) :5801-5804

[4]

FATIADI AJ, 1974, SYNTHESIS-STUTTGART, P229

[5] ABSOLUTE CONFIGURATION OF STEVIOL AND ISOSTEVIOL [J].

MOSETTIG, E ;

BEGLINGER, U ;

QUITT, P ;

DOLDER, F ;

LICHTI, H ;

WATERS, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (15) :2305-&

[6]

Ohloff G., 1982, FRAGRANCE CHEM, P535, DOI [10.1016/B978-0-12-685850-1.50020-6, DOI 10.1016/B978-0-12-685850-1.50020-6]

[7]

SELL C, 1990, CHEM IND, V20, P516

[8] ON TERPENES .137. ABSOLUTE CONFIGURATION OF NEROLIDOL [J].

VLAD, P ;

SOUCEK, M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1962, 27 (07) :1726-&

[9]

VLAD PF, 1989, CHEM ABSTR, V110

[10] ALLYLIC REARRANGEMENTS .19. STUDIES OF THE OZONIZATION OF ALLYLIC SYSTEMS [J].

YOUNG, WG ;

MCKINNIS, AC ;

WEBB, ID ;

ROBERTS, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (02) :293-296