Substituted 1,7-dioxabicyclo[3.3.0]octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

被引：42

作者：

Alonso, F ^{[1
]}

Lorenzo, E ^{[1
]}

Yus, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(97)00278-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 3-chloro-2-(chloromethyl)-1-propene(1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a -78 degrees C affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration-oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2(PPh(3))(3) (for aldehyde derivatives) yields the expected perhydrofurofurans 3. (C) 1997 Elsevier Science Ltd.

引用

页码：2187 / 2190

页数：4

共 31 条

[1] Arene-catalysed lithiation of triflates and triflamides under Barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds [J].

Alonso, E ;

Ramon, DJ ;

Yus, M .

TETRAHEDRON, 1996, 52 (45) :14341-14348

[2]

Blomberg C., 1993, The Barbier reaction and related one-step processes

[3]

BUCHI G, 1981, J AM CHEM SOC, V103, P3497, DOI 10.1021/ja00402a039

[4]

BUCHI G, 1967, J AM CHEM SOC, V89, P6745, DOI 10.1021/ja01001a062

[5]

Busby WF, 1984, ACS MONOGR SER, V182, P945

[6] SYNTHESES OF TETRAHYDROFURO[2,3-B]BENZOFURANS - A SYNTHESIS OF (H-AFLATOXIN-B2 [J].

CASTELLINO, AJ ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1006-1011

[7] Antibacterial neoclerodane diterpenoids from Ajuga lupulina [J].

Chen, H ;

Tan, RX ;

Liu, ZL ;

Zhang, Y ;

Yang, L .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (07) :668-670

[8] SYNTHESIS OF THE ENANTIOMERIC FUROBENZOFURANS, LATE PRECURSORS FOR THE SYNTHESIS OF (+)-AFLATOXINS AND (-)-AFLATOXINS B-1, B-2, G(1), AND G(2) [J].

CIVITELLO, ER ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3775-3782

[9]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[10]

*COUNC AGR SCI TEC, 1988, MYC EC HLTH RISKS

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