Total Synthesis and Structural Revision of the Cytotoxin Aruncin B

被引：19

作者：

Ribaucourt, Aubert ^{[1
]}

Hodgson, David M. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Mansfield Rd, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 17期

关键词：

DIOICUS VAR. KAMTSCHATICUS; GAMMA-ALKYLIDENEBUTENOLIDES; GUANACASTEPENE-A; ALPHA; TRITERPENOIDS; HETEROCYCLES; BUTENOLIDES; CYCLIZATION; METATHESIS; STRATEGIES;

D O I：

10.1021/acs.orglett.6b02120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sodium salts E-15 and Z-15 of the originally proposed dihydropyran acid structure of aruncin B (1) were prepared through ring-closing alkene metathesis (RCM) and ethoxygelenation-selenoxide elimination, but acid sensitivity of these salts, together with inconsistencies in the spectral data, suggested a significant structural misassignment. A beta-iodo Morita- Baylis-Hillman reaction to give Z-iodo ester 24, followed by Sonogashira cross-coupling-S-exo-dig lactonization, provided concise access to a Z-y-alkylidenebutenolide 18, which possessed data corresponding to those originally reported for aruncin B.

引用

页码：4364 / 4367

页数：4

共 42 条

[1] STRATEGIES FOR THE SYNTHESIS OF γ-ALKILIDENEBUTENOLIDES [J].

Almeida Barbosa, Luiz Claudio ;

Teixeira, Robson Ricardo ;

Pinheiro, Patricia Fontes ;

Alvares Maltha, Celia Regina ;

Demuner, Antonio Jacinto .

QUIMICA NOVA, 2010, 33 (05) :1163-1174

[2] Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks [J].

Austin, Kerrie A. B. ;

Elsworth, Jon D. ;

Banwell, Martin G. ;

Willis, Anthony C. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) :751-754

[3] Synthetic Strategies for the Preparation of Butenolides and Their Transformation into Other Derivatives [J].

Barbosa, Luiz C. A. ;

Teixeira, Robson R. ;

Amarante, Giovanni W. .

CURRENT ORGANIC SYNTHESIS, 2015, 12 (06) :746-771

[4] Novaxenicins A-D and xeniolides I-K, seven new diterpenes from the soft coral Xenia novaebrittanniae [J].

Bishara, Ashgan ;

Rudi, Amira ;

Goldberg, Israel ;

Benayahu, Yehuda ;

Kashman, Yoel .

TETRAHEDRON, 2006, 62 (51) :12092-12097

[5] The synthesis of γ-alkylidenebutenolides [J].

Brückner, R .

CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) :679-718

[6] Synthesis of symmetrical trisubstituted olefins by cross metathesis [J].

Chatterjee, AK ;

Sanders, DP ;

Grubbs, RH .

ORGANIC LETTERS, 2002, 4 (11) :1939-1942

[7] Insect toxins from spruce endophytes [J].

Findlay, JA ;

Li, GQ ;

Miller, JD ;

Womiloju, TO .

CANADIAN JOURNAL OF CHEMISTRY, 2003, 81 (04) :284-292

[8] Synthetic studies towards phomactin A. Concise synthesis of the novel tricyclic furanochroman system [J].

Foote, KM ;

Hayes, CJ ;

Pattenden, G .

TETRAHEDRON LETTERS, 1996, 37 (02) :275-278

[9]

Gambie C., 1999, AUST J CHEM, V52, P7

[10] FACTORS INFLUENCING THE NATURE OF SELENIRANIUM IONS IN SELENENYL CHLORIDE ADDITIONS TO ALKENES - THE USE OF METHANOL AS SOLVENT [J].

GARRATT, DG ;

KABO, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (10) :1030-1041

← 1 2 3 4 5 →