A Synthesis of the Carbocyclic Core of Maoecrystal V

被引：39

作者：

Lazarski, Kiel E. ^{[1
]}

Hu, Dennis X. ^{[1
]}

Stern, Charlotte L. ^{[1
]}

Thomson, Regan J. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

关键词：

INTRAMOLECULAR HYDROGEN ABSTRACTION; OXIDATION; GENERATION; ALPHA;

D O I：

10.1021/ol101025r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diets Alder reaction to forge the two contiguous quaternary stereocenters.

引用

页码：3010 / 3013

页数：4

共 27 条

[1] The development and use of ketene equivalents in [4+2] cycloadditions for organic synthesis [J].

Aggarwal, VK ;

Ali, A ;

Coogan, MP .

TETRAHEDRON, 1999, 55 (02) :293-312

[2]

Baeyer A., 1899, BER DTSCH CHEM GES, V32, P3625, DOI DOI 10.1002/CBER.189903203151

[3] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].

Ballini, R ;

Petrini, M .

TETRAHEDRON, 2004, 60 (05) :1017-1047

[4] IODOHYDRINS AND TETRAHYDROFURANS FROM LEAD TETRAACETATE-IODINE OXIDATION OF TERPENIC ALCOHOLS [J].

CECCHERELLI, P ;

CURINI, M ;

MARCOTULLIO, MC ;

MYLARI, BL ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1505-1509

[5] INTRAMOLECULAR HYDROGEN ABSTRACTION - IODOSOBENZENE DIACETATE, AN EFFICIENT AND CONVENIENT REAGENT FOR ALKOXY RADICAL GENERATION [J].

CONCEPCION, JI ;

FRANCISCO, CG ;

HERNANDEZ, R ;

SALAZAR, JA ;

SUAREZ, E .

TETRAHEDRON LETTERS, 1984, 25 (18) :1953-1956

[6] THE LOGIC OF CHEMICAL SYNTHESIS - MULTISTEP SYNTHESIS OF COMPLEX CARBOGENIC MOLECULES [J].

COREY, EJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :455-465

[7] TOTAL SYNTHESIS OF (+/-)-ANTHERIDIUM-INDUCING FACTOR (AAN,2) OF THE FERN ANEMIA PHYLLITIDIS - CLARIFICATION OF STEREOCHEMISTRY [J].

COREY, EJ ;

MYERS, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5574-5576

[8] SILICON-DIRECTED NAZAROV CYCLIZATION [J].

DENMARK, SE ;

JONES, TK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2642-2645

[9] INTRAMOLECULAR HYDROGEN ABSTRACTION - THE USE OF ORGANOSELENIUM REAGENTS FOR THE GENERATION OF ALKOXY RADICALS [J].

DORTA, RL ;

FRANCISCO, CG ;

FREIRE, R ;

SUAREZ, E .

TETRAHEDRON LETTERS, 1988, 29 (42) :5429-5432

[10] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

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