First Total Synthesis of Tanzawaic Acid B

Murata, Takatsugu; Tsutsui, Hisazumi; Yoshida, Takumi; Kubota, Hirokazu; Hiraishi, Shintaro; Natsukawa, Hiyo; Suzuki, Yuki; Hiraga, Daiki; Mori, Takahiro; Maekawa, Yutaro; Tateyama, Satoru; Toyoyama, Kiyotaka; Ito, Keiichi; Suzuki, Kyohei; Yonekura, Keita; Shibata, N.; Sato, Takaaki; Tasaki, Yasutaka; Inohana, Takehiko; Takano, Atsuhiro; Egashira, Naoki; Honda, Masaki; Umezaki, Yuma; Shiina, Isamu

doi:10.1021/acsomega.3c03634

Cited by 1 publication

(3 citation statements)

References 20 publications

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“…Shiina et al disclosed the first total synthesis of tanzawaic acid B (also named as GS-1302-1, 3, Scheme 2), [15] which is a natural product first isolated from Penicillium sp. GS1302, and later from different fungus, Penicillium citrinum, and more recently from a deep-sea derived Penicillium Species.…”

Section: Extension Of Evans' Chiral Auxiliary-based Asymmetric Synthe...mentioning

confidence: 99%

“…[16] Tanzawaic acids now constitute a small class of polyketide natural products characterized by a trans-decalin scaffold, which have been reported to exhibit diverse bioactivities including anticoccidial, cytotoxic, antifungal, antimalarial, and PTP1B inhibitory activities. [15,16] Shiina's synthesis of tanzawaic acid B relied on both the Evans asymmetric alkylation and asymmetric aldol reaction. After the Evans asymmetric alkylation reaction, the alkylation product 5 was reductively removed with lithium aluminum hydride (LAH) to yield alcohol 6, which was oxidized to give chiral aldehyde 7.…”

Section: Extension Of Evans' Chiral Auxiliary-based Asymmetric Synthe...mentioning

confidence: 99%

“…[67] This [4 + 2] cycloaddition prove to favor the endo-II pathway in the absence of viable bidentate coordination. It provides an efficient strategy for constructing enantioenriched isoquinuclidines prevalent motifs found in biologically active natural products such as catharanthine (15) and ibogaine (77).…”

Section: Chiral N-alkenyl-oxazolidinonesmentioning

confidence: 99%

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Evans’ Chiral Auxiliary‐Based Asymmetric Synthetic Methodology and Its Modern Extensions

Chen,

Huang

2023

Eur J Org Chem

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Although the asymmetric catalysis has made a spurt of progress, the use of chiral auxiliaries remains crucial in asymmetric synthesis due to both the reliability and versatility of the methods, and the predictability of stereochemistry of the reactions. Up to date, Evans’ chiral non‐racemic oxazolidinone‐based asymmetric synthetic methodology is still widely used in asymmetric synthesis. More importantly, the Evans asymmetric synthetic methodology turned out to be a fruitful source of inspiration for the development of related asymmetric synthetic methodologies. However, although reviews on the application of Evans’ asymmetric synthetic methodology in both organic synthesis and medicinal chemistry continually to appear in the literature, a comprehensive review dedicating to the extensions of Evans’ chiral non‐racemic oxazolidinone‐based asymmetric methodology remains elusive. In this review, we summarize the extensions of the Evans asymmetric methodology, which cover: (1) the modification of the chiral oxazolidinone auxiliaries; (2) the extension of the Evans’ asymmetric aldol reaction from Evans’ syn‐aldol to other diastereomeric aldol adducts; (3) the extension of the asymmetric reaction types; (4) the extension of chiral imide‐type substrates to N‐alkenyl, N‐allenenyl and N‐alkynyl oxazolidinones; (5) the achiral oxazolidinone‐based asymmetric catalysis; (6) the catalytic transformation of Evans’ products; and (7) the straightforward transformations of Evans’ chiral products to other classes of compounds than the chiral carboxylic acids, esters, alcohols, and Weinreb amides.

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Section: Extension Of Evans' Chiral Auxiliary-based Asymmetric Synthe...mentioning

confidence: 99%

Section: Extension Of Evans' Chiral Auxiliary-based Asymmetric Synthe...mentioning

confidence: 99%

See 1 more Smart Citation

Evans’ Chiral Auxiliary‐Based Asymmetric Synthetic Methodology and Its Modern Extensions

Chen,

Huang

2023

Eur J Org Chem

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First Total Synthesis of Tanzawaic Acid B

Cited by 1 publication

References 20 publications

Evans’ Chiral Auxiliary‐Based Asymmetric Synthetic Methodology and Its Modern Extensions

Evans’ Chiral Auxiliary‐Based Asymmetric Synthetic Methodology and Its Modern Extensions

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