Synthesis of Coronafacic Acid via TBAF-Assisted Elimination of the Mesylate and Its Conversion to the Isoleucine Conjugate

被引：4

作者：

Kosaki, Yusuke ^{[1
]}

Ogawa, Narihito ^{[1
]}

Wang, Qian ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

关键词：

ASYMMETRIC TOTAL SYNTHESES; PHYTOTOXIN CORONATINE; (+)-CORONAFACIC ACID; STEREOSELECTIVE-SYNTHESIS; METHYL JASMONATE; ANALOGS; BIOSYNTHESIS; ARABIDOPSIS; ACCUMULATION; CYCLIZATION;

D O I：

10.1021/ol201576c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An aldol reaction followed by elimination of the derived mesylate was used to construct the side chain that was designed to afford the cyclohexene ring of coronafacic acid via intramolecular alkylation. Elimination of the mesylate proceeded with TBAF. The alkylation was achieved with t-BuOK In THF, and then hydrolysis afforded coronafacic acid, which upon condensation with unprotected L-Isoleucine using CICO(2)Bu(I) furnished coronafacoyl-L-isoleucine, the L-lie conjugate.

引用

页码：4232 / 4235

页数：4

共 47 条

[1] Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues
Acharya, HP
Kobayashi, Y
[J]. TETRAHEDRON, 2006, 62 (14) : 3329 - 3343
[2] Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts
Arai, T
Sasai, H
Yamaguchi, K
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) : 441 - 442
[3] Structure-activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica Jacq.
Blechert, S
Bockelmann, C
Füsslein, M
Von Schrader, T
Stelmach, B
Niesel, U
Weiler, EW
[J]. PLANTA, 1999, 207 (03) : 470 - 479
[4] Browse J., 2009, REV PLANT BIOL, V60, P183
[5] Regulation of plant arginase by wounding, jasmonate, and the phytotoxin coronatine
Chen, H
McCaig, BC
Melotto, M
He, SY
Howe, GA
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (44) : 45998 - 46007
[6] The JAZ family of repressors is the missing link in jasmonate signalling
Chini, Andrea
Fonseca, S.
Fernandez, G.
Adie, B.
Chico, J. M.
Lorenzo, O.
Garcia-Casado, G.
Lopez-Vidriero, I.
Lozano, F. M.
Ponce, M. R.
Micol, J. L.
Solano, R.
[J]. NATURE, 2007, 448 (7154) : 666 - +
[7] Alternative splicing expands the repertoire of dominant JAZ repressors of jasmonate signaling
Chung, Hoo Sun
Cooke, Thomas F.
DePew, Cody L.
Patel, Lalita C.
Ogawa, Narihito
Kobayashi, Yuichi
Howe, Gregg A.
[J]. PLANT JOURNAL, 2010, 63 (04) : 613 - 622
[8] The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol
Curran, TT
Hay, DA
Koegel, CP
Evans, JC
[J]. TETRAHEDRON, 1997, 53 (06) : 1983 - 2004
[9] (+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate
Fonseca, Sandra
Chini, Andrea
Hamberg, Mats
Adie, Bruce
Porzel, Andrea
Kramell, Robert
Miersch, Otto
Wasternack, Claus
Solano, Roberto
[J]. NATURE CHEMICAL BIOLOGY, 2009, 5 (05) : 344 - 350
[10] Structure-activity relationships of synthetic analogs of jasmonic acid and coronatine on induction of benzo[c]phenanthridine alkaloid accumulation in Eschscholzia californica cell cultures
Haider, G
von Schrader, T
Füsslein, M
Blechert, S
Kutchan, TM
[J]. BIOLOGICAL CHEMISTRY, 2000, 381 (08) : 741 - 748

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