Remarkably complex and unpredictable cyclization and rearrangement reactions of cations derived from unsaturated oxiranes

被引：12

作者：

Corey, EJ ^{[1
]}

Roberts, BE ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10426-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis-acid catalyzed reactions of unsaturated epoxides 1 and 2 afford the unprecedented products 3 and 5, respectively. Mechanistic pathways for these reactions are presented (Schemes 2 and 4) along with a more fundamental analysis. (C) 1997 Elsevier Science Ltd.

引用

页码：8921 / 8924

页数：4

共 7 条

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[2] ENANTIOSELECTIVE TOTAL SYNTHESIS OF OLEANOLIC ACID, ERYTHRODIOL, BETA-AMYRIN, AND OTHER PENTACYCLIC TRITERPENES FROM A COMMON INTERMEDIATE
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[3] A new strategy for stereocontrol of cation-olefin cyclization. The first chemical emulation of the A/B-trans-9,10-syn-folding pathway of steroid biosynthesis from 2,3-oxidosqualene
Corey, EJ
Wood, HB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) : 11982 - 11983
[4] FIRST DEMONSTRATION OF A CARBOCATION-OLEFIN CYCLIZATION ROUTE TO THE LANOSTEROL SERIES
COREY, EJ
LEE, JM
LIU, DR
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9149 - 9152
[5] A short enantioselective total synthesis of dammarenediol II
Corey, EJ
Lin, SZ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) : 8765 - 8766
[6] Jenson C, 1997, SYNLETT, P518
[7] Sutherland J. K., 1991, COMP ORG SYNTH, V1, P341

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