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

Jun-Li Wang; Hui-Jing Li; Hong-Shuang Wang; Yan-Chao Wu

doi:10.1021/acs.orglett.7b01679

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

Org Lett. 2017 Jul 21;19(14):3811-3814. doi: 10.1021/acs.orglett.7b01679. Epub 2017 Jul 11.

Authors

Jun-Li Wang¹, Hui-Jing Li¹, Hong-Shuang Wang¹, Yan-Chao Wu^{1

2}

Affiliations

¹ School of Marine Science and Technology, Harbin Institute of Technology , Weihai 264209, China.
² Beijing National Laboratory for Molecular Sciences, ICCAS , Beijing 100190, China.

PMID: 28696127
DOI: 10.1021/acs.orglett.7b01679

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't