First total synthesis of the mastigophorenes C and D and of simplified unnatural analogs

被引：19

作者：

Bringmann, G ^{[1
]}

Pabst, T ^{[1
]}

Henschel, P ^{[1
]}

Michel, M ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

TETRAHEDRON | 2001年 / 57卷 / 07期

关键词：

mastigophorene C; mastigophorene D; natural products; sesquiterpenes;

D O I：

10.1016/S0040-4020(00)01131-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the mastigophorenes C (2) and D (3), natural 'dimeric' sesquiterpenes isolated from the livenwort Mastigophora diclados with interesting biological activities, is described. As previously for mastigophorenes A (1) and B, the divergent synthetic approach was first optimized on a simplified model system with a tert-butyl group instead of the chiral cyclopentyl residue, also in order to find more easily available compounds with similar or even improved biological activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1269 / 1275

页数：7

共 15 条

[1]

Asakawa Y, 1995, PROGR CHEM ORGANIC N, V65

[2] Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B [J].

Bringmann, G ;

Pabst, T ;

Henschel, P ;

Kraus, J ;

Peters, K ;

Peters, EM ;

Rycroft, DS ;

Connolly, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9127-9133

[3] Novel concepts in directed biaryl synthesis, part 89 - From dynamic to non-dynamic kinetic resolution of lactone-bridged biaryls: Synthesis of mastigophorene B [J].

Bringmann, G ;

Hinrichs, J ;

Pabst, T ;

Henschel, P ;

Peters, K ;

Peters, EM .

SYNTHESIS-STUTTGART, 2001, (01) :155-167

[4] Novel concepts in directed biaryl synthesis - Part 76 - First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol [J].

Bringmann, G ;

Pabst, T ;

Rycroft, DS ;

Connolly, JD .

TETRAHEDRON LETTERS, 1999, 40 (03) :483-486

[5] Atropo-enantioselective synthesis of a simplified analog of mastigophorenes A and B [J].

Bringmann, G ;

Pabst, T ;

Busemann, S ;

Peters, K ;

Peters, EM .

TETRAHEDRON, 1998, 54 (08) :1425-1438

[6] Herbertane sesquiterpenoids from the liverworts Herbertus aduncus and H-borealis [J].

Buchanan, MS ;

Connolly, JD ;

Rycroft, DS .

PHYTOCHEMISTRY, 1996, 43 (06) :1245-1248

[7]

DYKER G, 1998, EUR J ORG CHEM, P139

[8] MASTIGOPHORENES - NOVEL DIMERIC ISOCUPARANE-TYPE SESQUITERPENOIDS FROM THE LIVERWORT MASTIGOPHORA-DICLADOS [J].

FUKUYAMA, Y ;

TOYOTA, M ;

ASAKAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) :1341-1342

[9] NOVEL NEUROTROPHIC ISOCUPARANE-TYPE SESQUITERPENE DIMERS, MASTIGOPHORENES-A, MASTIGOPHORENE-B, MASTIGOPHORENE-C AND MASTIGOPHORENE-D, ISOLATED FROM THE LIVERWORT MASTIGOPHORA-DICLADOS [J].

FUKUYAMA, Y ;

ASAKAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2737-2741

[10]

Gille G, 2000, DRUG DEVELOP RES, V50, P153, DOI 10.1002/1098-2299(200006)50:2<153::AID-DDR4>3.0.CO

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