Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new lig...

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Bibliographic Details
Published in:Organic letters 2017-07, Vol.19 (14), p.3811-3814
Main Authors: Wang, Jun-Li, Li, Hui-Jing, Wang, Hong-Shuang, Wu, Yan-Chao
Format: Article
Language:English
Online Access:Get full text
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Summary:The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01679