Postulated Biogenesis-Guided Total Synthesis and Structural Revision of 2,18-seco-Lankacidinol A | Zendy

Kuan Zheng | Zendy; Ran Hong | Zendy

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Postulated Biogenesis-Guided Total Synthesis and Structural Revision of 2,18-seco-Lankacidinol A

Author(s) -

Kuan Zheng,

Ran Hong

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00993

Subject(s) - chemistry , diastereomer , stereochemistry , intramolecular force , ring (chemistry) , biogenesis , acetal , total synthesis , modular design , combinatorial chemistry , organic chemistry , biochemistry , computer science , programming language , gene

The macrocyclic structure of 2,18- seco -lankacidinol A, a newly isolated antitumor antibiotic, has been revised on the basis of a concise modular synthesis inspired by a reconsidered biosynthetic proposal. Notable features include (1) an acid-promoted intramolecular transacetalization of a N -lactoyl- O -methyl- N , O -acetal to construct the 4-oxazolidinone ring and (2) late-stage β-keto imide aldolizations that give rise to facile, stereodivergent access to all lactonic diastereomers.

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