- Synthesis of (±)-Bakuchiol via a pot-economy approach
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A rapid synthetic route toward (±)-Bakuchiol is presented in 29% overall yield. After the sole all-carbon quaternary carbon center is created via allylboration of 2-aryl acetaldehyde, a “Pot-Economy” approach including mesylation, elimination, and desilylation was realized in the presence oftBuOK under ambient temperature to provide (±)-Bakuchiol.
- Huang, Meng-Yuan,Chen, Long,Li, Ruoxi,Ji, Xueshun,Hong, Ran
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- Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis
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Asymmetric allylation of aldehydes with γ-disubstituted allyl halides has been achieved in the presence of a sulfonamide/oxazoline chromium complex. A variety of synthetically useful α-homoallylic alcohols with two consecutive stereogenic centers, including one quaternary carbon, can be accessed in a highly diastereoselective and enantioselective manner.
- Xiong, Yang,Zhang, Guozhu
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supporting information
p. 5094 - 5097
(2016/10/14)
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- A short synthesis of (+)-bakuchiol
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The concise enantioselective total synthesis of (+)-bakuchiol has been achieved using an asymmetric 1,4-addition to construct its all-carbon chiral quaternary center based on the induction of chirality by the (2′S)-2′-phenyloxazolidinone auxiliary, followed by a one-pot transformation under aldol reaction conditions. The synthesis was completed in four steps from (E)-geranic acid in an overall yield of 53%. Georg Thieme Verlag Stuttgart · New York.
- Esumi, Tomoyuki,Yamamoto, Chihiro,Fukuyama, Yoshiyasu
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p. 1845 - 1847
(2013/09/12)
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- A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol
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A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the α,β-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps.
- Xu, Qian-Qian,Zhao, Qun,Shan, Guang-Sheng,Yang, Xi-Cheng,Shi, Qi-Yuan,Lei, Xinsheng
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p. 10739 - 10746
(2013/12/04)
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- Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol
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An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.
- Takao, Ken-Ichi,Shu, Sakamoto,Touati, Marianne Ayaka,Kusakawa, Yusuke,Tadano, Kin-Ichi
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p. 13330 - 13344
(2013/02/23)
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- Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol
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The conjugate addition of lithium divinylcuprate to (4S,2′E)-3-(6′-TBDPS-3′-methylhex-2′-enoyl)-4-phenyloxazolidin-2-one proceeded efficiently to create a chiral all-carbon quaternary center with a high diastereoselectivity (R:S = 95:5). The absolute configuration of the newly generated chiral center was confirmed by applying this methodology to the total synthesis of (+)-bakuchiol.
- Esumi, Tomoyuki,Shimizu, Hiroyuki,Kashiyama, Akinori,Sasaki, Chizu,Toyota, Masao,Fukuyama, Yoshiyasu
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scheme or table
p. 6846 - 6849
(2009/04/07)
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- Stereoselective total synthesis of natural (S)-bakuchiol and its enantiomer
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A practical stereoselective synthesis of (S)-bakuchiol (1) and its enantiomer is reported. The important intermediate, (R)-configured β-siloxy aldehyde 5, was obtained in three steps from the easily available material geraniol (2) via the key step of Yamamoto's rearrangement of epoxy silyl ethers. (S)-Bakuchiol (1) and its enantiomer, (R)-bakuchiol (17), were finally obtained in different synthetic sequences with overall yields of 51% (ten steps) and 40% (nine steps) from geraniol (2), respectively.
- Du, Xiao-Long,Chen, Hong-Li,Feng, Hui-Jin,Li, Yuan-Chao
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experimental part
p. 371 - 378
(2009/02/07)
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- Synthesis and structure-immunosuppressive activity relationships of bakuchiol and its derivatives
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A series of derivatives of bakuchiol were synthesized and tested in vitro for their cytotoxicity, and inhibition of T cell proliferation and B cell proliferation. The data obtained provided preliminary structure-activity relationships of the compounds as immunosuppressive activity.
- Chen, Hongli,Du, Xiaolong,Tang, Wei,Zhou, Yu,Zuo, Jianping,Feng, Huijin,Li, Yuanchao
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p. 2403 - 2411
(2008/09/21)
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- Pharmaceutical compounds for treating copd
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Use of an MPO inhibitor for the treatment of COPD.
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- Enantiocontrolled synthesis of natural (+)-bakuchiol
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(+)-Bakuchiol (1), an irregular phenolic monoterpene of Psoralea corylifolia L., has been first synthesized in natural forms starting from (S)-O-benzylglycidol (2).
- Takano,Shimazaki,Ogasawara
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p. 3325 - 3326
(2007/10/02)
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