Combined multiple Claisen rearrangement and ring-closing metathesis as a route to naphthalene, anthracene, and anthracycline ring systems

被引：27

作者：

Chattopadhyay, SK ^{[1
]}

Pal, BK ^{[1
]}

Maity, S ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 12期

关键词：

D O I：

10.1246/cl.2003.1190

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

A new route involving double Claisen rearrangement of a suitable 1,4-diallyloxyarene system followed by ring-closing metathesis of the resulting diene has been developed for the synthesis of various benzannulated cyclohexenes. An important demonstration of this methodology is the construction of the tetracyclic quinophenolic ring system of the clinically important anthracyclines.

引用

收藏

页码：1190 / 1191

页数：2

相关论文

共 22 条

[1]

A general, stereocontrolled route to the geissoschizine family of alkaloids. Concise synthesis of the apogeissoschizine skeleton [J].

Birman, VB ;

Rawal, VH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9146-9147

[2]

EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .8. FUNCTIONALIZATION OF HYDROXYANTHRAQUINONES BY REDUCTIVE CLAISEN REARRANGEMENTS [J].

BODDY, IK ;

BONIFACE, PJ ;

CAMBIE, RC ;

CRAW, PA ;

HUANG, ZD ;

LARSEN, DS ;

MCDONALD, H ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (07) :1511-1529

[3]

EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .5. DOUBLE CLAISEN REARRANGEMENT OF 1,4-BIS(ALLYLOXY)ANTHRAQUINONES [J].

CAMBIE, RC ;

ZHENDONG, H ;

NOALL, WI ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) :819-828

[4]

Combined Claisen rearrangement and ring-closing metathesis as a route to oxepin- and oxocin-annulated coumarins [J].

Chattopadhyay, SK ;

Maity, S ;

Panja, S .

TETRAHEDRON LETTERS, 2002, 43 (43) :7781-7783

[5]

Davis CJ, 2002, SYNLETT, P1874

[6]

A new approach to functionalised spiropiperidines through tandem RCM and nitrogen-directed reactions [J].

Edwards, AS ;

Wybrow, RAJ ;

Johnstone, C ;

Adams, H ;

Harrity, JPA .

CHEMICAL COMMUNICATIONS, 2002, (14) :1542-1543

[7]

Sequential and cascade palladium catalysed cyclisation-anion capture-olefin metathesis [J].

Evans, P ;

Grigg, R ;

Ramzan, MI ;

Sridharan, V ;

York, M .

TETRAHEDRON LETTERS, 1999, 40 (15) :3021-3024

[8]

FIESER LOUIS F., 1939, JOUR AMER CHEM SOC, V61, P2206, DOI 10.1021/ja01877a068

[9]

A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction [J].

Huang, KS ;

Wang, EC .

TETRAHEDRON LETTERS, 2001, 42 (35) :6155-6157

[10]

KROHN K, 1990, TETRAHEDRON, V46, P291