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

Sylvain Henrion | Zendy; Aurélie Macé | Zendy; Margarita M. Vallejos | Zendy; Thierry Roisnel | Zendy; Bertrand Carboni | Zendy; José M. Villalgordo | Zendy; François Carreaux | Zendy

Open Access

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

Author(s) -

Sylvain Henrion,

Aurélie Macé,

Margarita M. Vallejos,

Thierry Roisnel,

Bertrand Carboni,

José M. Villalgordo,

François Carreaux

Publication year - 2018

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c8ob00101d

Subject(s) - chemistry , key (lock) , combinatorial chemistry , stereochemistry , operating system , computer science

An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-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 γ-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.

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