MERCURIC TRIFLUOROACETATE MEDIATED BROMINATIVE CYCLIZATIONS OF DIENES - TOTAL SYNTHESIS OF DL-3BETA-BROMO-8-EPICAPARRAPI OXIDE

被引：50

作者：

HOYE, TR

KURTH, MJ

机构：

[1] Department of Chemistry, University of Minnesota, Minneapolis

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 20期

关键词：

D O I：

10.1021/jo01334a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mercuric trifluoroacetate induces the electrophilic cyclization of homogeranic acid and diene alcohols 10 with concomitant carbon-carbon bond formation to generate the bicyclic organomercury compounds 2 and 12. The mercury substituent can be stereospecifically replaced by bromine with either retention or inversion of configuration to give the bromides 1 or 4 and 11 or 14, respectively. Application of this net brominative cyclization to a synthesis of dl-3β-bromo-8-epicaparrapi oxide (15) in seven steps and 12% yield from geranylacetone is described. © 1979, American Chemical Society. All rights reserved.

引用

页码：3461 / 3467

页数：7

共 48 条

[1] BAKER JB, 1976, COMPOUNDS MARINE ORG
[2] SOME METABOLITES FROM AUSTRALIAN MARINE ORGANISMS
BAKER, JT
[J]. PURE AND APPLIED CHEMISTRY, 1976, 48 (01) : 35 - 44
[3] ACID CATALYSIS OF CLAISEN REARRANGEMENT .1. FORMATION OF 4,4'-BIS (2H-CHROMENYL)MERCURY DERIVATIVES FROM ARYL 2-PROPYNYL ETHERS
BATES, DK
JONES, MC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) : 3775 - 3776
[4] SYNTHESIS OF SEVERAL 3,4-METHYLENEDIOXYPHENYL DERIVATIVES AS INHIBITORS FOR METAMORPHOSIS OF SILKWORM LARVAE
CHANG, CF
TAMURA, S
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1972, 36 (13): : 2405 - 2410
[5] SPECTRA AND STEROCHEMISTRY .7. LONG-RANGE SHIELDING BY NITRILE GROUPS
CROSS, AD
HARRISON, IT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (20) : 3223 - &
[6] DYADCHENKO AI, 1976, IAN SSSR KH, P2276
[7] DYADCHENKO AI, 1976, IZV AN SSSR K, P2281
[8] ZUR KENNTNIS DER TRITERPENE .190. EINE STEREOCHEMISCHE INTERPRETATION DER BIOGENETISCHEN ISOPRENREGEL BEI DEN TRITERPENEN
ESCHENMOSER, A
RUZICKA, L
JEGER, O
ARIGONI, D
[J]. HELVETICA CHIMICA ACTA, 1955, 38 (07) : 1890 - 1904
[9] 3BETA-BROMO-8-EPICAPARRAPI OXIDE, MAJOR METABOLITE OF LAURENCIA-OBTUSA
FAULKNER, DJ
[J]. PHYTOCHEMISTRY, 1976, 15 (12) : 1992 - 1993
[10] BIOMIMETIC SYNTHESIS OF MARINE NATURAL-PRODUCTS
FAULKNER, DJ
[J]. PURE AND APPLIED CHEMISTRY, 1976, 48 (01) : 25 - 28

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