Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone with cycloalkenyl silyl ethers for the synthesis of bicarbocycles

被引：20

作者：

Cho, CG ^{[1
]}

Kim, YW ^{[1
]}

Kim, WK ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 46期

关键词：

Diels-Alder cycloaddition; 2-pyrones; carbocycles; dienes; lactone;

D O I：

10.1016/S0040-4039(01)01760-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,5-Dibromo-2-pyrone underwent facile Diels-Alder [4+2] cycloadditions with cycloalkenyl silyl ethers to provide a series of tricyclolactones, with good to excellent chemical yields and stereoselectivity. The resulting cycloadducts could be readily converted into the corresponding bicarbocycles upon selective debromination and reductive lactone ring opening reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8193 / 8195

页数：3

共 18 条

[1] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES
AFARINKIA, K
VINADER, V
NELSON, TD
POSNER, GH
[J]. TETRAHEDRON, 1992, 48 (42) : 9111 - 9171
[2] Eurycolactones A-C, novel quassinoids from Eurycoma longifolia
Ang, HH
Hitotsuyanagi, Y
Takeya, K
[J]. TETRAHEDRON LETTERS, 2000, 41 (35) : 6849 - 6853
[3] Boyer FD, 2000, SYNTHESIS-STUTTGART, P1868
[4] One step preparation of bromo-2-pyrones via bromo-decarboxylation of 2-pyrone-carboxylic acids
Cho, CG
Park, JS
Jung, IH
Lee, H
[J]. TETRAHEDRON LETTERS, 2001, 42 (06) : 1065 - 1067
[5] CHO CG, 2001, IN PRESS J ORG CHEM
[6] KVITA V, 1992, CHIMIA, V46, P457
[7] KVITA V, 1993, CHIMIA, V47, P3
[8] A mild method for ring-opening aminolysis of lactones
Liu, WM
Xu, DD
Repic, O
Blacklock, TJ
[J]. TETRAHEDRON LETTERS, 2001, 42 (13) : 2439 - 2441
[9] TOTAL SYNTHESIS OF TAXOL
NICOLAOU, KC
YANG, Z
LIU, JJ
UENO, H
NANTERMET, PG
GUY, RK
CLAIBORNE, CF
RENAUD, J
COULADOUROS, EA
PAULVANNAN, K
SORENSEN, EJ
[J]. NATURE, 1994, 367 (6464) : 630 - 634
[10] Asymmetric synthesis of the key intermediate of an SP antagonist RPR107880 using a base-catalyzed Diels-Alder reaction
Okamura, H
Shimizu, H
Nakamura, Y
Iwagawa, T
Nakatani, M
[J]. TETRAHEDRON LETTERS, 2000, 41 (21) : 4147 - 4150

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