958885-86-4Relevant 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.
Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B
Boukouvalas, John,Wang, Jian-Xin,Marion, Olivier,Ndzi, Bruno
, p. 6670 - 6673 (2007/10/03)
Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.