Total Syntheses of Rhodomollins A and B

The first and asymmetric total syntheses of rhodomollins A and B, two rhodomollane type grayanoids featuring a d-homograyanane carbon skeleton and an oxa-bicyclo­[3.2.1] core, were accomplished via a convergent strategy. A Stille coupling and a lithium-halogen exchange/intramolecular nucleophilic ad...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-12, Vol.145 (49), p.27160-27166
Main Authors: Zhao, Weizhao, Zhang, Duo, Wang, Yuran, Yang, Ming
Format: Article
Language:English
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Summary:The first and asymmetric total syntheses of rhodomollins A and B, two rhodomollane type grayanoids featuring a d-homograyanane carbon skeleton and an oxa-bicyclo­[3.2.1] core, were accomplished via a convergent strategy. A Stille coupling and a lithium-halogen exchange/intramolecular nucleophilic addition to the aldehyde sequence were employed to assemble two enantioenriched fragments. The oxa-bicyclo­[3.2.1] core was achieved through an intramolecular SN2 substitution of cyclic sulfate of 1,2-diols (Williamson ether synthesis). The A ring oxidation states were adjusted by a Payne/Meinwald rearrangement sequence and subsequent redox transformations.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c12249