Rapid and practical synthesis of (−)-1-deoxyaltronojirimycin

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

“…Five-membered dihydrofuran rings lead to the synthesis of furanomycin D [35–36], norfuranomycin E [37], and the polyoxin family F [38]. The six-membered tetrahydropyridine G synthesized via this route can be used as an intermediate in the synthesis of iminosugars, e.g., of the deoxynojirimycin family H [39–43]. The trans -allylic alcohol C contains already the functional groups of sphingosines and depending on the stereochemistry at C 2 and C 3 , the synthesis of all four isomers can be achieved [44–47].…”

Diastereoselective synthesis of vicinal amino alcohols

“…Three more operations led to the target structure 79. 27 We had a hypothesis, that a Z-vinyl lithium species would offer higher selectivity on the basis that it is sterically more demanding than the bullet-like acetylene. Unfortunately, it was found to behave in similar fashion to lithium acetylenes, as noted during the synthesis of jaspine B (81) and its diastereomers (Scheme 20).…”

Scalable synthesis of (−)-trans-3-hydroxypipecolic acid via a useful chiral building block

“…Reagents were obtained from Scheme 1. Reagents and conditions: a) HC^CCH 2 OTBS, n-BuLi, THF, À78 C, then 4; b) NaH, BnBr, NaI, DMF/THF, 0 C; c) NH 4 …”

“…The synthesis is a modified and streamlined version of the synthesis we used to synthesize deoxyaltronojirimycin. 4 …”