Asymmetric synthesis of trans-4,5-disubstituted gamma-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin

作者：Henrion S; Mace A; Vallejos M M; Roisnel T; Carboni B; Villalgordo J M; Carreaux F^*

来源：Organic and Biomolecular Chemistry, 2018, 16(10): 1672-1678.

DOI：10.1039/c8ob00101d

An efficient asymmetric synthesis of trans-4,5-disubstituted gamma-butyrolactones from aldehydes and enantioenriched gamma-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse gamma-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.

• 出版日期2018-3-14