Synthesis of the cyclohexan subunit of baconipyrones A and B from furan

被引：35

作者：

Arjona, O ^{[1
]}

Menchaca, R ^{[1
]}

Plumet, J ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 01期

关键词：

D O I：

10.1021/ol000334t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of the cyclohexan subunit of the siphonariid metabolites baconipyrones A and B from furan is described. A key step included the alkylative ring opening of 7-oxanorbornenic sulfone 4 and oxidative desulfonylation of compound 8.

引用

页码：107 / 109

页数：3

共 14 条

[1] SULFONE DIRECTED ALKYLATIVE BRIDGE CLEAVAGE OF OXABICYCLIC VINYL SULFONES WITH ORGANOLITHIUM REAGENTS [J].

ARJONA, O ;

DEDIOS, A ;

DELAPRADILLA, RF ;

PLUMET, J ;

VISO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3906-3916

[2] REGIOSELECTIVITY OF ELECTROPHILIC ADDITIONS TO 7-OXABICYCLO[2.2.1]HEPTENES CONTROLLED BY REMOTE SUBSTITUENTS - ARENESULFONYL SUBSTITUTED 7-OXABICYCLO[2.2.1]HEPTENES AS STEREOSELECTIVE AND REGIOSELECTIVE CHIRAL DIENOPHILES [J].

BLACK, KA ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5341-5348

[3] New non-contiguous polypropionates from marine molluscs: A comment on their natural product status [J].

Brecknell, DJ ;

Collett, LA ;

Davies-Coleman, MT ;

Garson, MJ ;

Jones, DD .

TETRAHEDRON, 2000, 56 (16) :2497-2502

[4]

Davies-Colman MT, 1998, NAT PROD REP, V15, P477

[5] THE TRIMETHYLSILYL CATIONIC SPECIES AS A BULKY PROTON - APPLICATION TO CHEMOSELECTIVE DIOXOLANATION [J].

HWU, JR ;

WETZEL, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3946-3948

[6] GENERAL SCOPE OF 1,3-DIOXOLANATION OF ALPHA,BETA-UNSATURATED ALDEHYDES WITH 1,2-BIS((TRIMETHYLSILYL)OXY)ETHANE AND TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE [J].

HWU, JR ;

LEU, LC ;

ROBL, JA ;

ANDERSON, DA ;

WETZEL, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :188-191

[7] THE BACONIPYRONES - NOVEL POLYPROPIONATES FROM THE PULMONATE SIPHONARIA-BACONI [J].

MANKER, DC ;

FAULKNER, DJ ;

STOUT, TJ ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5371-5374

[8] Cerium(III) chloride, a novel reagent for nonaqueous selective conversion of dioxolanes to carbonyl compounds [J].

Marcantoni, E ;

Nobili, F ;

Bartoli, G ;

Bosco, M ;

Sambri, L .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4183-4184

[9] Studies in marine polypropionate synthesis:: Total synthesis of (-)-baconipyrone C [J].

Paterson, I ;

Chen, DYK ;

Aceña, JL ;

Franklin, AS .

ORGANIC LETTERS, 2000, 2 (11) :1513-1516

[10] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF THE SIPHONARINS AND BACONIPYRONES - ENANTIOCONTROLLED SYNTHESIS OF A GAMMA-PYRONE SUBUNIT [J].

PATERSON, I ;

FRANKLIN, AS .

TETRAHEDRON LETTERS, 1994, 35 (37) :6925-6928

← 1 2 →