Rearrangement of a tricyclic 2,5-cyclohexadienone: Towards a general synthetic route to the daphnanes and (+)-resiniferatoxin

被引：0

作者：

Jackson, SR ^{[1
]}

Johnson, MG ^{[1
]}

Mikami, M ^{[1
]}

Shiokawa, S ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2001年 / 40卷 / 14期

关键词：

D O I：

10.1002/1521-3773(20010716)40:14<2694::AID-ANIE2694>3.0.CO;2-D

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5-cyclohexadienone subunit within a complex tricyclic ring system (see scheme). The chemistry we describe should not only find use in the total synthesis of resiniferatoxin and related daphnanes, but should also provide useful templates for access to complex analogues.

引用

页码：2694 / 2697

页数：4

共 50 条

[1] MECHANISTIC ORGANIC PHOTOCHEMISTRY .21. ELECTRONIC DETAILS OF 2,5-CYCLOHEXADIENONE REARRANGEMENT
ZIMMERMAN, HE
SWENTON, JS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (04) : 906 - +
[2] UNPRECEDENTED REARRANGEMENT PRODUCTS FROM ULTRAVIOLET-IRRADIATION OF A MODEL 2,5-CYCLOHEXADIENONE
SCHUSTER, DI
SMITH, KJ
BRISIMITZAKIS, AC
VANDERVEEN, JM
GRUSKA, RP
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02): : 473 - 478
[3] CHEMISTRY OF 2-METHOXY-2,5-CYCLOHEXADIENONE .4. PHOTOCHEMISTRY OF 2-METHOXY-4,4-DIPHENYL-2,5-CYCLOHEXADIENONE AND 4-DICHLOROMETHYL-2-METHOXY-4-METHYL-2,5-CYCLOHEXADIENONE
MATOBA, K
KAWAGOSHI, F
TANABE, M
YAMAZAKI, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (09) : 3709 - 3714
[4] ENANTIODIVERGENT PREPARATION OF CHIRAL 2,5-CYCLOHEXADIENONE SYNTHONS
TAKANO, S
HIGASHI, Y
KAMIKUBO, T
MORIYA, M
OGASAWARA, K
SYNTHESIS-STUTTGART, 1993, (10): : 948 - 950
[5] RADICAL FRAGMENTATION ROUTE ON PHOTOLYSIS OF 2,5-CYCLOHEXADIENONES . 4-METHYL-4-TRICHLOROMETHYL-2,5-CYCLOHEXADIENONE
SCHUSTER, DI
PATEL, DJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (11) : 2515 - &
[6] PHOTOCHEMICAL-REARRANGEMENT OF 4,4-DISUBSTITUTED-4-SILA-2,5-CYCLOHEXADIENONE
KOCH, TH
SODERQUI.JA
KINSTLE, TH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1974, : 115 - 115
[7] OBSERVATION OF A KETYL RADICAL ON FLASH EXCITATION OF A 2,5-CYCLOHEXADIENONE
SCHUSTER, DI
BARILE, GC
TETRAHEDRON LETTERS, 1976, (35) : 3017 - 3020
[8] [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons
Lange, GL
Humber, CC
Manthorpe, JM
TETRAHEDRON-ASYMMETRY, 2002, 13 (13) : 1355 - 1362
[9] CONTROL OF STEREOCHEMISTRY OF 2,5-CYCLOHEXADIENONE PHOTOISOMERIZATION BY STERIC FACTORS
RODGERS, TR
HART, H
TETRAHEDRON LETTERS, 1969, (55) : 4845 - &
[10] CHEMISTRY OF 2-METHOXY-2,5-CYCLOHEXADIENONE .5. PHOTOCHEMICAL-REARRANGEMENT AND OXIDATION OF 2-METHOXY-4-METHYL-4-PHENYL-2-CYCLOHEXENONE AND 2-METHOXY-4-METHYL-4-PHENYL-2,5-CYCLOHEXADIENONE
MATOBA, K
NODA, H
YAMAZAKI, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (07) : 2627 - 2634

← 1 2 3 4 5 →