Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

Zaragoza Ramon J.; Gonzalez-Cardenete Miguel A.

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Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

机译：致力酸A和B的合成，C-18和C-19官能化的海叶萜类替代素：抗铝反应的DFT研究

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The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.

机译：已经开发了通过Aldol反应的C-18-和C-19-双官能化的上萜类二萜类萜类二萜类萜类二萜类二萜类化合物，并且已经开发出通过醛醇反应。这种关键的Aldol反应对空间障碍非常敏感。氘交换实验和DFT方法研究了这一事实。优化该反应导致合成抗炎致力酸A和B，原酸原始。

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《RSC Advances》 |2020年第25期|共8页
作者
Zaragoza Ramon J.; Gonzalez-Cardenete Miguel A.;
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Univ Valencia Dept Quim Organ Dr Moliner 50 E-46100 Valencia Spain;

Univ Politecn Valencia Inst Tecnol Quim CSIC Avda Narattios S-N E-46022 Valencia Spain;

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正文语种 eng
中图分类化学;
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1. Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction [J] . Zaragoza Ramon J., Gonzalez-Cardenete Miguel A. RSC Advances . 2020,第25期

机译：致力酸A和B的合成，C-18和C-19官能化的海叶萜类替代素：抗铝反应的DFT研究
2. Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction [J] . Ramón J. Zaragozá, Miguel A. González-Cardenete RSC Advances . 2020,第25期

机译：致力酸A和B的合成，C-18和C-19官能化的海叶萜类替代素：抗铝反应的DFT研究
3. Study for diastereoselective aldol reaction in flow: synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid, a key component of cyclodepsipeptide HDAC inhibitors [J] . Doi Takayuki, Otaka Hiroyuki, Umeda Koji, Tetrahedron . 2015,第37期

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4. Theoretical Study of the Diels-Alder Reaction in the Synthesis of Abietane Diterpenes [C] . Du Rui-huan, Zheng Bai-qin, Zhang Jian-min International Conference on Computer-Aided Design, Manufacturing, Modeling and Simulation . 2014

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5. Novel cinchona alkaloid derived ammonium salts as phase-transfer catalysts for the asymmetric synthesis of beta-hydroxy alpha-amino acids via aldol reactions and total synthesis of celogentin C. [D] . Ma, Bing. 2009

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6. Diastereoselectivity in Lewis-Acid Catalyzed Mukaiyama Aldol Reactions: A DFT Study [O] . Joshua M. Lee, Paul Helquist, Olaf Wiest -1

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7. Diastereoselectivity in Lewis-Acid-Catalyzed Mukaiyama Aldol Reactions: A DFT Study [O] . Joshua M. Lee, Paul Helquist, Olaf Wiest 2012

机译：Lewis-酸催化的Mukaiyama aldol反应的非对映选择性：DFT研究

Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

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