21019-64-7

Upstream product

• 139126-09-3 2-((1R,2R,3R)-2-Hydroxy-1,2,3-trimethyl-cyclopentyl)-5-methyl-phenol 
• 139126-06-0 (3aR,8bR)-3,6,8b-Trimethyl-1,2,3,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3a-ol 
• 139125-95-4 (3aR,8bR)-3,6,8b-Trimethyl-1,2,3,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3a-ylamine 
• 125029-56-3 4-Bromo-2-((1R,2R,3R)-2-hydroxy-1,2,3-trimethyl-cyclopentyl)-5-methyl-phenol 
• 63087-74-1 (+/-)-3a-epi-debromoaplysin 
• 125029-57-4 C₂₉H₂₉BrO₄ 

Relevant academic research and scientific papers

The rearrangement of some cyclopentanone-aryloximes: Synthesis of (±)-aplysin, (±)-filiformin and of their debromo analogues

Upon acid catalyzed rearrangement after Sheradsky, the aryloximes A gave the tricyclic aminals C, which suffered hydrolysis to lactols E. The unique alcohol 29 was then prepared through a highly stereoselective equilibration-reductive alkylation of the epimeric mixture of lactols 22a,b. Two routes, one of which was stereospecific, allowed cyclization of 29 to (±)-aplysin 34. The yield was 2.5 % from oximes 2a,b. The isomeric epi-aplysin 35 and filiformin 36 were also obtained from 29. The debromo analogues 37,38 and 39 and their trideutero derivatives 41,42 and 43 were synthesized along similar line and allowed unequivocal structure elucidation by NMR spectroscopy.

THE SHERADSKY REARRANGEMENT OF α,α-DISUBSTITUTED CYCLOPENTANONE ARYLOXIMES: A SYNTHESIS OF THE SESQUITERPENES (+/-)-APLYSIN AND (+/-)-FILIFORMIN

Lactols 6a,b, obtained by the Sheradsky rearrangement of aryloximes o, were alkylated in to 9a, in which three contiguous chiral centers were controlled.Cyclization of 9a gave the marine sesquiterpenes (+/-)-aplysin 11 and (+/-)-filiformin 13.