A carbohydrate-based approach for the total synthesis of sawaranospirolide C

Yu, Shuai; Liu, Yinxin; Shang, Chengxiang; Du, Yuguo; Li, Jun

doi:10.1016/j.tetlet.2021.153072

Cited by 4 publications

(1 citation statement)

References 22 publications

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“…Considering the impressive broad-band biological activities of brevipolides and their potential medicinal application, we sought to develop an enantioselective synthesis of brevipolides. As part of our ongoing research program on the total synthesis of biologically active natural products using carbohydrate as chiral pool, [10][11][12][13] herein, we describe a concise and stereoselective synthesis of natural (+)-brevipolide H (8) from D-galactal and ethyl Llactate.…”

Section: Paper Synthesismentioning

confidence: 99%

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

Zhao

Geng

et al. 2021

Synthesis

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The efficient and concise synthesis of cytotoxic 5, 6-dihydro-α-pyrone (+)-brevipolide H has been accomplished in 12 long linear steps with 8.65% overall yield from readily available chiral synthons, D-galactal and L-ethyl lactate. The features of this synthesis are highly diastereoselective Simmons-Smith cyclopropanation and carbohydrate-based chiron approach to rapid access to key 5, 6-dihydro-α-pyrone skeleton.

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Section: Paper Synthesismentioning

confidence: 99%

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

Zhao

Geng

et al. 2021

Synthesis

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Total Synthesis of Spiroalkaloids Lycibarbarines A–C

et al. 2023

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The concise and efficient synthesis of tetrahydroquinoline alkaloids lycibarbarines A−C has been accomplished in four steps from a common intermediate derived from commercially available 2‐deoxy‐D‐ribose and 8‐hydroxyquinoline. For the synthesis of the unique tetracyclic spiro‐heterocycle skeleton we employed a synthetic strategy that features two key transformations: iodomethyllithium‐based homologation of lactone / N‐alkylation to access tetracyclic spiro‐heterocycle skeleton in one step and one‐pot acetonide deprotection, hemiacetal formation, and spirocyclization cascade process.

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Total synthesis of cryptopyranmoscatone B2

Zhao

Nie

et al. 2022

Tetrahedron

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A carbohydrate-based approach for the total synthesis of sawaranospirolide C

Cited by 4 publications

References 22 publications

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

Total Synthesis of Spiroalkaloids Lycibarbarines A–C

Total synthesis of cryptopyranmoscatone B2

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