Synthesis of bicyclic ketals related to zaragozic acid by a novel photoannulation

被引：18

作者：

FreemanCook, KD ^{[1
]}

Halcomb, RL ^{[1
]}

机构：

[1] UNIV COLORADO,DEPT CHEM & BIOCHEM,BOULDER,CO 80309

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 28期

关键词：

D O I：

10.1016/0040-4039(96)01001-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,8-dioxabicyclo[3.2.1]octane ring system of the zaragozic acids was synthesized by a Norrish Type II photochemical reaction. This reaction occured through an unusual 1,6-hydrogen abstraction to generate a 1,5-biradical. A solvent study found that using benzene provides the best yield of the desired cyclized product. Copyright (C) 1996 Elsevier science Ltd

引用

页码：4883 / 4886

页数：4

共 27 条

[1] SYNTHESIS OF A NOVEL SPIROCYCLIC LACTONE IN A POTENTIAL ROUTE TO SQUALESTATIN-1
ABDELRAHMAN, H
ADAMS, JP
BOYES, AL
KELLY, MJ
LAMONT, RB
MANSFIELD, DJ
PROCOPIOU, PA
ROBERTS, SM
SLEE, DH
WATSON, NS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (10): : 1259 - 1261
[2] SYNTHESIS OF THE BICYCLIC CORE STRUCTURE OF SQUALESTATIN-1
ABDELRAHMAN, H
ADAMS, JP
BOYES, AL
KELLY, MJ
MANSFIELD, DJ
PROCOPIOU, PA
ROBERTS, SM
SLEE, DH
SIDEBOTTOM, PJ
SIK, V
WATSON, NS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) : 1841 - 1843
[3] A SYNTHETIC APPROACH TO SQUALESTATIN-1
ABDELRAHMAN, H
ADAMS, JP
BOYES, AL
KELLY, MJ
MANSFIELD, DJ
PROCOPIOU, PA
ROBERTS, SM
SLEE, DH
WATSON, NS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) : 1839 - 1841
[4] AGGARWAL VK, 1994, J CHEM SOC CHEM COMM, V87
[5] BAXTER A, 1992, J BIOL CHEM, V267, P11705
[6] ACCURATE CALCULATIONS OF REACTIVITIES AND DIASTEREOSELECTIVITIES IN COMPLEX-MOLECULES - AN AM1 STUDY OF 1,3-DIOXOLAN-4-ONES AND RELATED OXYGEN HETEROCYCLES
BECKWITH, ALJ
ZAVITSAS, AA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) : 607 - 614
[7] ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE
BERGSTROM, JD
KURTZ, MM
REW, DJ
AMEND, AM
KARKAS, JD
BOSTEDOR, RG
BANSAL, VS
DUFRESNE, C
VANMIDDLESWORTH, FL
HENSENS, OD
LIESCH, JM
ZINK, DL
WILSON, KE
ONISHI, J
MILLIGAN, JA
BILLS, G
KAPLAN, L
OMSTEAD, MN
JENKINS, RG
HUANG, L
MEINZ, MS
QUINN, L
BURG, RW
KONG, YL
MOCHALES, S
MOJENA, M
MARTIN, I
PELAEZ, F
DIEZ, MT
ALBERTS, AW
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) : 80 - 84
[8] INTRAMOLECULAR HYDROGEN-ATOM ABSTRACTION - THE BETA-OXYGEN EFFECT IN THE NORRISH TYPE-II PHOTOREACTION
BRUNCKOVA, J
CRICH, D
[J]. TETRAHEDRON, 1995, 51 (44) : 11945 - 11952
[9] PHOTOCHEMICAL EPSILON-HYDROGEN ABSTRACTION AS A ROUTE TO TETRAHYDROPYRAN-3-OLS
CARLESS, HAJ
FEKARURHOBO, GK
[J]. TETRAHEDRON LETTERS, 1984, 25 (51) : 5943 - 5946
[10] SYNTHESIS OF 1-SUBSTITUTED AND 1,4-DISUBSTITUTED 2,3-DI-O-BENZYL-1,6-ANHYDROGALACTOFURANOSES
CARON, S
MCDONALD, AI
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) : 2780 - 2785

← 1 2 3 →