INTRAMOLECULAR ALDER ENE APPROACH TO STEREOCHEMICAL CONTROL OVER 3 CONTIGUOUS STEREOGENIC CENTERS - SYNTHESIS OF (+/-)-METHYL CUCURBATE AND (+/-)-METHYL EPIJASMONATE

被引：16

作者：

SARKAR, TK ^{[1
]}

GHORAI, BK ^{[1
]}

BANERJI, A ^{[1
]}

机构：

[1] BHABHA ATOM RES CTR, DIV BIOORGAN, MODULAR LAB, BOMBAY 400085, INDIA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 37期

关键词：

D O I：

10.1016/0040-4039(94)85038-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of epijasmonoids, (+/-)-methyl cucurbate and (+/-)-methyl epijasmonate is described starting from aldehyde 14, where the key step is a highly stereocontrolled 5- (3,4) ene cyclization 17 --> 18.

引用

页码：6907 / 6908

页数：2

共 23 条

[1] Stereochemical control over three contiguous stereogenic centers in the intramolecular ene reaction of activated 1,6-dienes. Application to the synthesis of (+/-)-methyl cucurbate and (+/-)-methyl epijasmonate
Sarkar, TK
Ghorai, BK
Nandy, SK
Mukherjee, B
Banerji, A
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17): : 6006 - 6011
[2] Stereochemical Control over Three Contiguous Stereogenic Centers in the Intramolecular Ene Reaction of Activated 1,6-Dienes. Application to the Synthesis of (n)-Methyl Cucurbate and (n)-Methyl Epijasmonate
J Org Chem, 17 (6006):
[3] INTRAMOLECULAR ALDER ENE REACTION OF ACTIVATED 1,6-DIENES - STEREOCHEMICAL CONTROL OVER 3 CONTIGUOUS STEREOGENIC CENTERS
SARKAR, TK
GHORAI, BK
NANDY, SK
MUKHERJEE, B
TETRAHEDRON LETTERS, 1994, 35 (37) : 6903 - 6906
[4] INTRAMOLECULAR ENE APPROACH TO STEREOCONTROL OVER 3 CONTIGUOUS CHIRAL CENTERS
MIKAMI, K
TAKAHASHI, K
NAKAI, T
TETRAHEDRON LETTERS, 1989, 30 (03) : 357 - 360
[5] Intramolecular Ene Approach to Carbocyclization with Stereocontrol over Four Contiguous Chiral Centers: An Efficient Access to Iridoids
Mikami, Koichi
Takahashi, Kazuhiko
Nakai, Takeshi
SYNLETT, 1989, (01) : 45 - 46
[6] Diels-Alder modification of monoterpenes and Alder-ene synthesis involving 3-methyl-3-cyanocyclopropene
R. V. Ashirov
S. A. Appolonova
V. V. Plemenkov
Chemistry of Natural Compounds, 2006, 42 : 434 - 438
[7] Diels-Alder modification of monoterpenes and Alder-ene synthesis involving 3-methyl-3-cyanocyclopropene
Ashirov, R. V.
Appolonova, S. A.
Plemenkov, V. V.
CHEMISTRY OF NATURAL COMPOUNDS, 2006, 42 (04) : 434 - 438
[8] STUDIES ON THE TOTAL SYNTHESIS OF CHLOROTHRICOLIDE - STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF METHYL UNDECA-2,8,10-TRIENOATES
ROUSH, WR
HALL, SE
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (17) : 5200 - 5211
[9] INTRAMOLECULAR HYDROSILYLATIONS .3. ASYMMETRIC INDUCTION IN THE INTRAMOLECULAR HYDROSILYLATION OF 2-METHYL-3-DI-ISOPROPYLSILYLOXYHEPT-1-ENE - A STEREOSELECTIVE SYNTHESIS OF SYN-2-METHYLHEPTANE-1,3-DIOL
ANWAR, S
DAVIS, AP
PROCEEDINGS OF THE ROYAL IRISH ACADEMY SECTION B-BIOLOGICAL GEOLOGICAL AND CHEMICAL SCIENCE, 1989, 89 (6-52) : 71 - 78
[10] Synthesis, crystal structure and intramolecular interactions of 2-methyl-3-(2-methylphenyl)but-1-ene-1, 1-dicarbonitrile (MMBD)
Grabowski, SJ
Wilamowski, J
Osman, D
Sepiol, JJ
Rodier, N
AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (09) : 951 - 954

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