Total Synthesis of the Antitumor Antibiotic Basidalin | Zendy

Jaime A. M. Acosta | Zendy; Ramesh Muddala | Zendy; Luiz C. A. Barbosa | Zendy; John Boukouvalas | Zendy

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Total Synthesis of the Antitumor Antibiotic Basidalin

Author(s) -

Jaime A. M. Acosta,

Ramesh Muddala,

Luiz C. A. Barbosa,

John Boukouvalas

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b01255

Subject(s) - dithiane , aldol condensation , yield (engineering) , antibiotics , aldol reaction , total synthesis , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , physics , biochemistry , thermodynamics

The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.

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