Preparation of optically active 2-furylcarbinols by kinetic resolution using the Sharpless reagent and their application in organic synthesis

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

“…In the original Achmatowicz approach, the furfuryl carbinol is oxidized with bromine in the presence of methanol under weakly basic conditions. Many other modifications of the original Achmatowicz procedure, such as oxidation of the furan ring with m -CPBA [18], dimethyldioxirane [19], NBS [20,21], tert -BuOOH\VO(OAc) 2 [22], or H 2 O 2 -titanium silicalite [23], have also been used for this transformation. This route has the advantage that the original configuration of the alcohol moiety in the furylcarbinol is preserved and, therefore, the method is amenable to the preparation of both d - and l -series [24,25,26].…”

The Chromium(II)-Mediated Coupling of Secondary Alkylhalides with Aromatic Aldehydes

“…Benzaldehyde was distilled from potassium hydride. Spectral data of the known compounds 3a, 14 3b, 15 3c, 16 , 3d, 17 , 3e, 18 Copyright of Synlett is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use.…”

A Formal Total Synthesis of (+)‐Frondosin A

“…Oxidative conversion of the furan ring of 4 into the corresponding pyran ring in the presence of another olefin was accomplished by selective oxidation of the furan ring using Sharpless epoxidation conditions for allylic alcohols . The obtained diastereomeric mixture of pyranol was acetylated and was treated with base to form oxidopyrylium ion 3 .…”