38011-83-5Relevant articles and documents
Scalable Total Synthesis of rac-Jungermannenones B and C
Liu, Weilong,Li, Houhua,Cai, Pei-Jun,Wang, Zhen,Yu, Zhi-Xiang,Lei, Xiaoguang
, p. 3112 - 3116 (2016)
Reported is the first scalable synthesis of rac-jungermannenones B and C starting from the commercially available and inexpensive geraniol in 10 and 9 steps, respectively. The unique jungermannenone framework is rapidly assembled by an unprecedented regio
Practical and Efficient Strategy for Synthesis of Ferruginol, Sugiol, and Sugiol Methyl Ether from Geraniol
Oh, Seong Taek,Kim, Taejung,Kim, Youngseok,Lee, Sin-Ae,Jahng, Yurngdong,Ham, Jungyeob,Park, Jae Gyu
, p. 1015 - 1018 (2018/08/17)
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Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes
Tao, Zhonglin,Robb, Kevin A.,Zhao, Kuo,Denmark, Scott E.
supporting information, p. 3569 - 3573 (2018/03/21)
A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.