Synthesis of d,l-norlabdane oxide and related odorants:: An intramolecular radical approach

被引：24

作者：

Zoretic, PA ^{[1
]}

Fang, HQ

Ribeiro, AA

机构：

[1] E Carolina Univ, Dept Chem, Greenville, NC 27858 USA

[2] Duke Univ, Med Ctr, Duke NMR Spect Ctr, Durham, NC 27710 USA

[3] Duke Univ, Med Ctr, Dept Radiol, Durham, NC 27710 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 14期

关键词：

D O I：

10.1021/jo980211a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cascade radical approach to d,l-norlabdane oxide and related odorants is reported. Oxidative radical cyclization of polyene 4 with Mn(III) and Cu(II) afforded exclusively bicycle 3, which upon acid treatment gave tricycle 2 possessing the norlabdane oxide skeleton with a.modified A-ring system. Tricycle 2 was ultimately converted to d,l-norlabdane oxide 1 and to several new A-ring labdane oxides as potential odorants.

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页码：4779 / 4785

页数：7

相关论文

共 44 条

[1] FORMAL SYNTHESIS OF (+/-)-AMBROX(R) [J].

BARCO, A ;

BENETTI, S ;

BIANCHI, A ;

CASOLARI, A ;

GUARNERI, M ;

POLLINI, GP .

TETRAHEDRON, 1995, 51 (30) :8333-8338

[2]

BARNES AG, Patent No. 3439564

[3] SYNTHESIS OF NOR-AMBREINOLIDE FROM (+)-CIS-ABIENOL [J].

BARRERO, AF ;

SANCHEZ, JF ;

ALVAREZMANZANEDA, EJ ;

ALTAREJOS, J ;

MUNOZ, M ;

HAIDOUR, A .

TETRAHEDRON, 1994, 50 (22) :6653-6662

[4] 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

[5] SYNTHESIS OF AMBROX(R) FROM COMMUNIC ACIDS [J].

BARRERO, AF ;

ALTAREJOS, J ;

ALVAREZMANZANEDA, EJ ;

RAMOS, JM ;

SALIDO, S .

TETRAHEDRON, 1993, 49 (28) :6251-6262

[6] AMBER-TYPE ODORANTS FROM COMMUNIC ACIDS [J].

BARRERO, AF ;

ALTAREJOS, J ;

ALVAREZMANZANEDA, EJ ;

RAMOS, JM ;

SALIDO, S .

TETRAHEDRON, 1993, 49 (42) :9525-9534

[7] Synthesis of (+/-)-ambrox from (E)-nerolidol and beta-ionone via allylic alcohol [2,3] sigmatropic rearrangement [J].

Barrero, AF ;

Altarejos, J ;

AlvarezManzaneda, EJ ;

Ramos, JM ;

Salido, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2215-2218

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

BARTON, DHR ;

TAYLOR, DK ;

TSE, C .

TETRAHEDRON LETTERS, 1994, 35 (51) :9505-9508

[9] 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

[10]

BARTON DHR, 1991, SYNTHESIS-STUTTGART, P743

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