Asymmetric Total Synthesis of (−)-Spirochensilide A

Liang, Xinting; Chen, Jiahua; Yang, Zhen

doi:10.1021/jacs.0c02522

Cited by 45 publications

(46 citation statements)

References 74 publications

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“…In 2020, Chen and Yang's group proposed an elegant total synthesis of (−)-spirochensilide A. 24 During their early-stage synthesis, a two-step epoxidation/semipinacol ring-contraction consequence has been developed to convert a trans -octahydronaphthalene system 15 to an octahydroindene carbocycle 17 with vicinal quaternary carbon centers ( Scheme 5 ). Of note, only a single diastereoisomer was obtained in the rearrangement reaction of 16 , indicating a highly regio- and diastereochemical control of the ring-contraction process, and the aldehyde functionality introduced through the rearrangement could be further elaborated as a functional handle.…”

Section: Epoxidesmentioning

confidence: 99%

Recent development and applications of semipinacol rearrangement reactions

Zhang

Wang

et al. 2021

Chem. Sci.

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Section: Epoxidesmentioning

confidence: 99%

Recent development and applications of semipinacol rearrangement reactions

Zhang

Wang

et al. 2021

Chem. Sci.

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“…[62] Yang and coworkers demonstrated the first stereoselective total synthesis of (À )-spirochensilide A (Scheme 21). [63] This synthesis incorporates semipinacol rearrangement, tungstenassisted cyclopropene-centered Pauson-Khand reaction, and oxidative ring formation reaction of furan to build the spiroketal entity, stereoselectively.…”

Section: (à )-Sinularianin B (14)mentioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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“…Higher base loading causes a faster reaction and lower enantioselectivity (Scheme 52). [114] During the investigation of ring-opening annulation reaction Matsuda et al found that base mediated ring-opening annulation of cyclopropenone and carbonyl or ester is extensively studied but the same reaction with amide or aldehyde remains unexplored. They developed a silver triflate catalyzed ring-opening [3 + 2] annulation reaction of 258 and 259 to give 260 in good yield.…”

Section: Miscellaneousmentioning

confidence: 99%