Application of a new nucleophilic addition/ring closure (NARC) sequence to the synthesis of enantiomerically-pure 2,8-dioxabicyclo[3.2.1]octanes of relevance to the squalestatins and zaragozic acids

被引：13

作者：

Fallon, GD ^{[1
]}

Jones, ED ^{[1
]}

Perlmutter, P ^{[1
]}

Selajarern, W ^{[1
]}

机构：

[1] Monash Univ, Dept Chem, Clayton, Vic 3168, Australia

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(99)01523-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

PL rapid method for the enantioselective construction of 2,8-dioxabicyclo[3.2.1]octanes of relevance to the zaragozic acids, employing a tandem NARC sequence of aldol and intramolecular Wacker reactions, is described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：7435 / 7438

页数：4

共 35 条

[1] Total synthesis of (+)-zaragozic acid C
Armstrong, A
Jones, LH
Barsanti, PA
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3337 - 3340
[2] DISCOVERY, BIOSYNTHESIS, AND MECHANISM OF ACTION OF THE ZARAGOZIC ACIDS - POTENT INHIBITORS OF SQUALENE SYNTHASE
BERGSTROM, JD
DUFRESNE, C
BILLS, GF
NALLINOMSTEAD, M
BYRNE, K
[J]. ANNUAL REVIEW OF MICROBIOLOGY, 1995, 49 : 607 - 639
[3] N-acetylbornane-10,2-sultam: A useful, enantiomerically pure acetate synthon for asymmetric aldol reactions
Bond, S
Perlmutter, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) : 6397 - 6400
[4] Remote allylic silyloxy groups as stereocontrol elements in intramolecular oxymercurations of gamma-hydroxyalkenes
Bratt, K
Garavelas, A
Perlmutter, P
Westman, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) : 2109 - 2117
[5] Preparation of the zaragozic acid core through the rearrangement of an oxonium ylide
Brogan, JB
Zercher, CK
[J]. TETRAHEDRON LETTERS, 1998, 39 (13) : 1691 - 1694
[6] PALLADIUM-CATALYZED SYNTHESIS OF ENDO-BREVICOMIN AND EXO-BREVICOMIN AND RELATED DI-OXABICYCLO[X.2.1] AND TRI-OXABICYCLO[X.2.1]SYSTEMS
BYROM, NT
GRIGG, R
KONGKATHIP, B
REIMER, G
WADE, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1643 - 1653
[7] Total synthesis of zaragozic acid A (squalestatin S1). Synthesis of the relay compound
Caron, S
Stoermer, D
Mapp, AK
Heathcock, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9126 - 9134
[8] CHAIN C, 1996, TETRAHEDRON LETT, V37, P8925
[9] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206
EVANS, DA
BENDER, SL
MORRIS, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) : 2506 - 2526
[10] Synthesis of bicyclic ketals related to zaragozic acid by a novel photoannulation
FreemanCook, KD
Halcomb, RL
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4883 - 4886

← 1 2 3 4 →