A simple, ring-closing metathesis reaction based approach to (±)-1,14-herbertenediol and (±)-11-epi-herbertenolide

被引：27

作者：

Srikrishna, A ^{[1
]}

Rao, MS ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(01)02051-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of 1,14-herbertenediol via 11-epi-herbertenolide. and a formal total synthesis of tochuinyl acetate and dihydrotochuinyl acetate, employing a ring-closing metathesis reaction based methodology, are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：151 / 154

页数：4

共 18 条

[1] Enantioselective synthesis of herbertane sesquiterpenes.: Synthesis of (-)-herbertene and (-)-α-herbertenol [J].

Abad, A ;

Agulló, C ;

Cuñat, AC ;

Perni, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1741-1744

[2] Total syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)-mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines [J].

Degnan, AP ;

Meyers, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2762-2769

[3]

Eicher T, 1996, SYNTHESIS-STUTTGART, P863

[4] Total syntheses of neuroprotective mastigophorenes A and B [J].

Fukuyama, Y ;

Matsumoto, K ;

Tonoi, Y ;

Yokoyama, R ;

Takahashi, H ;

Minami, H ;

Okazaki, H ;

Mitsumoto, Y .

TETRAHEDRON, 2001, 57 (33) :7127-7135

[5] Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts [J].

Fukuyama, Y ;

Kiriyama, Y ;

Kodama, M .

TETRAHEDRON LETTERS, 1996, 37 (08) :1261-1264

[6]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[7] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[8] New total synthesis of (±)-herbertene, (±)-β-herbertenol and (±)-herbertenediol [J].

Gupta, PD ;

Pal, A ;

Roy, A ;

Mukherjee, D .

TETRAHEDRON LETTERS, 2000, 41 (39) :7563-7566

[9] 1,5-diketones from 3,4-dihydropyranones:: An application in the synthesis of (±)-α-herbertenol [J].

Harrowven, DC ;

Hannam, JC .

TETRAHEDRON, 1999, 55 (30) :9333-9340

[10] A short synthesis of α-herbertenol featuring the use of a dihydropyranone as a 1,5-diketone synthon [J].

Harrowven, DC ;

Hannam, JC .

TETRAHEDRON LETTERS, 1998, 39 (51) :9573-9574

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