Computational study on the reaction mechanism of the key thermal [4+4] cycloaddition reaction in the biosynthesis of epoxytwinol A

被引：7

作者：

Shiina, I ^{[1
]}

Uchimaru, T

Shoji, M

Kakeya, H

Osada, H

Hayashi, Y

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

[3] Natl Inst Adv Ind Sci & Technol, Res Inst Computat Sci, Tsukuba, Ibaraki 3058658, Japan

[4] RIKEN, Discovery Res Inst, Antibiot Lab, Wako, Saitama 3510198, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 06期

关键词：

D O I：

10.1021/ol052916m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The key [4 + 4] cycloaddition in the biosynthesis of epoxytwinol A has been established by theoretical calculations to comprise of three processes. The first step is formation of the C8-C8' bond generating a biradical intermediate. Next, rotation about the C8-C8' bond occurs, and finally the C1-C1' bond is formed. Biradicals stabilized by conjugation and two hydrogen bonds are essential for realization of this rare thermal [4 + 4] cycloaddition.

引用

页码：1041 / 1044

页数：4

共 50 条

[21] Reaction Mechanism of an Intramolecular Oxime Transfer Reaction: A Computational Study
Moilanen, Jani
Neuvonen, Antti
Pihko, Petri
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (05): : 2006 - 2014
[22] Enzymatic Stetter Reaction: Computational Study of the Reaction Mechanism of MenD
Planas, Ferran
McLeish, Michael J.
Himo, Fahmi
ACS CATALYSIS, 2021, 11 (19) : 12355 - 12366
[23] Regioselective Molecularly Imprinted Reaction Field for [4+4] Photocyclodimerization of 2-Anthracenecarboxylic
Nakai, Satoshi
Sunayama, Hirobumi
Kitayama, Yukiya
Nishijima, Masaki
Wada, Takehiko
Inoue, Yoshihisa
Takeuchi, Toshifumi
LANGMUIR, 2017, 33 (09) : 2103 - 2108
[24] Investigation of the reaction mechanism of [4
Kostiv, Irina
FRENCH-UKRAINIAN JOURNAL OF CHEMISTRY, 2018, 6 (01): : 74 - 81
[25] Computational study of the thermal reaction rate between S+(4S) and acetylene
Aschi, M
Largo, A
CHEMICAL PHYSICS, 2001, 265 (03) : 251 - 261
[26] ABINITIO STUDY ON THE MECHANISM OF CYCLOADDITION REACTION OF KETENE WITH METHYLENIMINE - A NEW REACTION SCHEME
FANG, DC
FU, XY
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1992, 43 (05) : 669 - 676
[27] Theoretical study on mechanism of cycloaddition reaction of difluorosilylene with formaldehyde
Lu, XH
Wang, YX
Liu, CB
Deng, CH
ACTA PHYSICO-CHIMICA SINICA, 1999, 15 (01) : 78 - 81
[28] AN ABINITIO STUDY ON THE MECHANISM OF THE KETENE IMINE CYCLOADDITION REACTION
SORDO, JA
GONZALEZ, J
SORDO, TL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) : 6249 - 6251
[29] STUDIES ON BAUDISCH REACTION .4. REACTION MECHANISM
MARUYAMA, K
TANIMOTO, I
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (11) : 3120 - +
[30] ON THE JACOBSEN REACTION .4. CHARACTER AND REACTION MECHANISM
SUZUKI, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1963, 36 (12) : 1642 - 1650

← 1 2 3 4 5 →