EPOXIDE-INITIATED CATIONIC POLYENE CYCLIZATIONS

被引：41

作者：

FISH, PV ^{[1
]}

SUDHAKAR, AR ^{[1
]}

JOHNSON, WS ^{[1
]}

机构：

[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)61492-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid (2-propoxy)titanium trichloride is an efficient reagent for epoxide-initiated polyene cyclisations. Thus, 4 underwent tricyclisation to yield tricyclic products 5-7 in 73 % yield. The tetraene epoxide 1 gave pentacycle 15 in 21 % yield. The latter is the first example of a cationic pentacarbocyclisalion.

引用

页码：7849 / 7852

页数：4

共 30 条

[1] CHAWLA A, 1967, TETRAHEDRON LETT, P4837
[2] COREY EJ, 1967, TETRAHEDRON LETT, P2325
[3] AN EFFECTIVE SYSTEM FOR EPOXIDE-INITIATED CATION-OLEFIN CYCLIZATION
COREY, EJ
SODEOKA, M
[J]. TETRAHEDRON LETTERS, 1991, 32 (48) : 7005 - 7008
[4] CYCLIZATION OF EPOXYOLEFINS - REACTION OF GERANIOLENE MONOEPOXIDE WITH BORON FLUORIDE ETHERATE
GOLDSMITH, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (20) : 3913 - &
[5] STRUCTURAL AND STEREOCHEMICAL COURSE OF IN VITRO EPOXY OLEFIN CYCLIZATION . DITERPENOID INTERMEDIATES
GOLDSMITH, DJ
PHILLIPS, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) : 5862 - +
[6] ITO S, 1974, NATURAL PRODUCTS CHE, V1, P365
[7] CATION-STABILIZING AUXILIARIES IN POLYENE CYCLIZATIONS .5. THE FLUORINE ATOM AS A CATION-STABILIZING AUXILIARY IN BIOMIMETIC POLYENE CYCLIZATIONS .2. ASYMMETRIC-SYNTHESIS OF A STEROID
JOHNSON, WS
FLETCHER, VR
CHENERA, B
BARTLETT, WR
THAM, FS
KULLNIG, RK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 497 - 504
[8] A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE
JOHNSON, WS
WERTHEMANN, L
BARTLETT, WR
BROCKSOM, TJ
LI, TT
FAULKNER, DJ
PETERSEN, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 741 - +
[9] CATION-STABILIZING AUXILIARIES IN POLYENE CYCLIZATIONS .6. THE FLUORINE ATOM AS A CATION-STABILIZING AUXILIARY IN BIOMIMETIC POLYENE CYCLIZATIONS .3. USE TO EFFECT REGIOSPECIFIC CONTROL
JOHNSON, WS
BUCHANAN, RA
BARTLETT, WR
THAM, FS
KULLNIG, RK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 504 - 515
[10] CATION-STABILIZING AUXILIARIES IN POLYENE CYCLIZATIONS .4. THE FLUORINE ATOM AS A CATION-STABILIZING AUXILIARY IN BIOMIMETIC POLYENE CYCLIZATIONS .1. BACKGROUND AND EXPLORATORY EXPERIMENTS
JOHNSON, WS
CHENERA, B
THAM, FS
KULLNIG, RK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 493 - 497

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