A SHORT AND EFFICIENT SYNTHESIS OF (-)-AMBROX(R) FROM (-)-SCLAREOL USING A RUTHENIUM OXIDE CATALYZED KEY STEP

被引：35

作者：

MARTRES, P ^{[1
]}

PERFETTI, P ^{[1
]}

ZAHRA, JP ^{[1
]}

WAEGELL, B ^{[1
]}

GIRAUDI, E ^{[1
]}

PETRZILKA, M ^{[1
]}

机构：

[1] CTR RECH GIVAUDAN ROURE,F-06332 GRASSE,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 04期

关键词：

AMBROX(R); SCLAREOL; RUTHENIUM TETROXIDE;

D O I：

10.1016/S0040-4039(00)61637-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Ambrox(R)5 has been synthesized in 3 steps from natural (-)-sclareol 1. Depending on the reoxidizing agents and the reaction conditions used in the ruthenium oxide catalyzed key step, overall yields of 79% (NaIO4/RuO4) or 48% (Ca(OCl)2/RuO4-) were observed.

引用

页码：629 / 632

页数：4

共 38 条

[11] GARNERO J, 1977, 7TH INT C ESS OILS K, P479
[12] GONZALEZSIERRA M, 1987, HETEROCYCLES, V26, P2801
[13] ODEUR ET CONSTITUTION .4. SUR LES EPOXYDES HYDROAROMATIQUES A ODEUR AMBREE
HINDER, M
STOLL, M
[J]. HELVETICA CHIMICA ACTA, 1950, 33 (05) : 1308 - 1312
[14] SYNTHESIS OF (-)-AMBROX FROM L-ABIETIC ACID
KOYAMA, H
KAKU, Y
OHNO, M
[J]. TETRAHEDRON LETTERS, 1987, 28 (25) : 2863 - 2866
[15] ADAPTATION OF OXYANIONIC SIGMATROPY TO THE CONVERGENT ENANTIOSELECTIVE SYNTHESIS OF AMBERGRIS-TYPE ODORANTS
MALECZKA, RE
PAQUETTE, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6538 - 6546
[16] MARTRES P, 1991, THESIS U AIX MARSEIL
[17] Maurey H. W., 1962, United States Patent, Patent No. [3050532A, 3050532]
[18] MOOKHERJEE B D, 1990, Perfumer and Flavorist, V15, P27
[19] MOOKHERJEE BD, 1977, 7TH INT C ESS OILS K
[20] MORI K, 1990, LIEBIGS ANN CHEM, P361

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