550334-72-0

Upstream product

• 550334-68-4 2-(5E,7E)-(nona-5,7-diene-1-yl)-1,3-dioxolane 
• 550334-60-6 (R)-4-benzyl-3-((2E,8E,10E)-dodeca-2,8,10-trienoyl)-oxazolidin-2-one 
• 95019-19-5 (2-[(N-benzylprolyl)amino]benzophenone) 
• 57006-69-6 (E,E)-sorbyl acetate 

Downstream Products

• 454473-87-1 (1R,2R,4aR,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthalene-1-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of an Isomer of the Decalinoyltetramic Acid Methiosetin by a Stereocontrolled IMDA Reaction of a Metal-Chelated 3-Trienoyltetramate

An isomer of the 3-decalinoyltetramic acid methiosetin was synthesized for the first time. The decalin moiety was established by a late-stage intramolecular Diels-Alder cyclization catalyzed by Me2AlCl or La(OTf)3. Its high diastereoselectivity arose from stereoinduction by a well-defined metal O,O-chelate complex of the 3-acyltetramic acid moiety. The nature of the metal and the bulkiness of the residues at the tetramic acid chelator are decisive for the stereochemical outcome.

Toward the synthesis of tetrodecamycin: Asymmetric synthesis of a direct precursor of the C6-C18 trans-decalin portion

We report the asymmetric synthesis of a direct precursor of the C6-C18 trans-decalin portion of tetrodecamycin utilising an asymmetric intramolecular Diels-Alder (IMDA) reaction as the key step.