A convenient synthesis of (+)-albicanol based on enzymatic function: total syntheses of (+)-albicanyl acetate, (-)-albicanyl 3,4-dihydroxycinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox

被引：53

作者：

Akita, H ^{[1
]}

Nozawa, M ^{[1
]}

Mitsuda, A ^{[1
]}

Ohsawa, H ^{[1
]}

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(00)00076-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By using lipase 'PL-266' from Alcaligenes sp. enantioselective acetylation of (+/-)-albicanol 4 with isopropenyl acetate gave the enantiomerically pure (+)-albicanyl acetate 3 and (+)-albicanol 4. Deprotection of (+)-3 afforded the natural (+)-albicanol 4 which was converted to the natural products (-)-albicanyl 3,4-dihydroxycinnamate 7, (-)-drimenol 8, (-)-drimenin 9 and (-)-ambrox 10. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1375 / 1388

页数：14

共 17 条

[1] Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol
Akita, H
Nozawa, M
Shimizu, H
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (10) : 1789 - 1799
[2] THE CONSTITUTION AND STEROCHEMISTRY OF DRIMENOL, A NOVEL BICYCLIC SESQUITERPENOID
APPEL, HH
BROOKS, CJW
OVERTON, KH
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (NOV): : 3322 - 3332
[3] SESQUITERPENOIDS .2. THE CONSTITUTION AND STEREOCHEMISTRY OF DRIMENIN, ISODRIMENIN, AND CONFERTIFOLIN
APPEL, HH
CONNOLLY, JD
OVERTON, KH
BOND, RPM
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (NOV): : 4685 - 4692
[4] SYNTHESIS OF BIOLOGICALLY-ACTIVE DRIMANES AND HOMODRIMANES FROM (-)-SCLAREOL
BARRERO, AF
MANZANEDA, EA
ALTAREJOS, J
SALIDO, S
RAMOS, JM
SIMMONDS, MSJ
BLANEY, WM
[J]. TETRAHEDRON, 1995, 51 (27) : 7435 - 7450
[5] SYNTHESIS OF BIOLOGICALLY-ACTIVE DRIMANES FROM (-)-SCLAREOL
BARRERO, AF
ALVAREZMANZANEDA, E
ALTAREJOS, J
SALIDO, S
RAMOS, JM
[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2945 - 2948
[6] SYNTHESIS OF (-)-UGANDENSIDIAL
CORTES, M
RAZMILIC, I
LOPEZ, J
[J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (05): : 1369 - 1371
[7] CORTES MJ, 1985, CHEM IND-LONDON, P735
[8] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[9] TERPENOIDS FROM THE DORID NUDIBRANCH CADLINA-LUTEOMARGINATA
HELLOU, J
ANDERSEN, RJ
THOMPSON, JE
[J]. TETRAHEDRON, 1982, 38 (13) : 1875 - 1879
[10] THE SYNTHESIS OF DRIMANE SESQUITERPENOIDS
JANSEN, BJM
DEGROOT, A
[J]. NATURAL PRODUCT REPORTS, 1991, 8 (03) : 319 - 337

← 1 2 →