88862-14-0Relevant articles and documents
Lewis Acid-Catalyzed Stereoselective α-Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides
Adamkiewicz, Anna,W?glarz, Izabela,Butkiewicz, Aleksandra,Woyciechowska, Marta,Mlynarski, Jacek
, p. 667 - 678 (2019/12/24)
The stereoselective α-addition to cyclic dienol silanes has rarely been exploited, in contrast to the well-studied γ-addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α-addition of 2-trimetylsiloxy furan to optically pure aldehydes in water-containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural products: vitexolide D, curcucomosin C, villosin, chinensine C, (+)-coronarin E and (E)-labda-7,11,13-trien-16,15-olid.
Formal Total Synthesis of Actinoranone and Asymmetric Synthesis of Labda-7,13-(E)-dien-15-ol
Novaes, Luiz F.T.,Pastre, Julio C.
, p. 3163 - 3166 (2017/06/23)
The syntheses of the polyketide and terpenoid fragments of actinoranone are reported in a concise fashion, relying on catalytic methods. Minimization on the use of protecting groups and redox reactions allowed the synthesis of the carbon backbone of actin
Straightforward synthesis of the strong ambergris odorant γ-bicyclohomofarnesal and its endo-isomer from R-(+)-sclareolide
De La Torre, María C.,García, Isabel,Sierra, Miguel A.
, p. 6351 - 6353 (2007/10/03)
γ-Bicyclohomofarnesal 1 and its endo isomer 5 were prepared in 47 and 26% overall yields, respectively, from commercial R-(+)-sclareolide (7), in a three-step sequence. The synthetic procedure involves the preparation of Weinreb's amide 9, dehydration of tertiary alcohol to form compounds 10 and 11, chromatographic separation and reduction with LiAlH4. This approach is simple and can compete with the syntheses previously reported for the preparation of these important compounds, both in overall yields and in the number of synthetic steps.
