Formal synthesis of degraded sterol (+)-aplykurodinone-1

Singh, Nishant ; Pulukuri, Kiran Kumar ; Chakraborty, Tushar Kanti (2015) Formal synthesis of degraded sterol (+)-aplykurodinone-1 Tetrahedron, 71 (28). pp. 4608-4615. ISSN 00404020

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Official URL: http://doi.org/10.1016/j.tet.2015.05.026

Related URL: http://dx.doi.org/10.1016/j.tet.2015.05.026

Abstract

The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodolactonization reactions for the synthesis of the final tricyclic precursor of the target molecule.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Ltd
Keywords:Asymmetric Sharpless kinetic resolution;Cp2Ti(III)Cl, radical cyclization;Ring closing metathesis (RCM)Eschenmoser-Claisen rearrangement;Iodolactonization
ID Code:131101
Deposited On:02 Dec 2022 10:34
Last Modified:02 Dec 2022 10:34

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