Preparation of the zaragozic acid core through the rearrangement of an oxonium ylide

被引：33

作者：

Brogan, JB ^{[1
]}

Zercher, CK ^{[1
]}

机构：

[1] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(98)00127-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective formation of a 2,8-dioxabicyclo[3.2.1]octane skeleton was accomplished through the generation and rearrangement of a bicyclic oxonium ylide. The skeleton which was formed is common to the zangozic acid family and possesses appropriate functionality for further manipulation. The study also revealed the first example of an exocyclic 2,3-shift from a acetal-derived oxonium ylide. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1691 / 1694

页数：4

共 26 条

[1] ARMSTRONG A, 1995, SYNLETT, P903
[2] BAXTER A, 1992, J BIOL CHEM, V267, P11705
[3] 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
[4] Study of the rearrangements of oxonium ylides generated from ketals
Brogan, JB
Zercher, CK
Bauer, CB
Rogers, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) : 3902 - 3909
[5] Selectivity in the rearrangements of oxonium ylides
Brogan, JB
Bauer, CB
Rogers, RD
Zercher, CK
[J]. TETRAHEDRON LETTERS, 1996, 37 (29) : 5053 - 5056
[6] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS
BROOKS, DW
LU, LDL
MASAMUNE, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01): : 72 - 74
[7] 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
[8] SYNTHESIS OF (+)-ZARAGOZIC ACID-C
CARREIRA, EM
DUBOIS, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) : 10825 - 10826
[9] SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES
CLARK, JS
KROWIAK, SA
STREET, LJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (27) : 4385 - 4388
[10] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY
DAWSON, MJ
FARTHING, JE
MARSHALL, PS
MIDDLETON, RF
ONEILL, MJ
SHUTTLEWORTH, A
STYLLI, C
TAIT, RM
TAYLOR, PM
WILDMAN, HG
BUSS, AD
LANGLEY, D
HAYES, MV
[J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (05) : 639 - 647

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