97042-20-1

Upstream product

• 152715-31-6 <3R-(3aα,5aS,7aα,11aβ,11bα)>-(+)-methyl 1,3,3a,6,7,7a,8,9,10,11,11a,11b-dodecahydro-6α-hydroxy-8,8,11a-trimethyl-2H-cyclobuta-phenanthrene-3β-carboxylate 
• 152715-34-9 <3R-(3aα,5aS,7aα,11aβ,11bα)>-(-)-methyl 6α-butyroxy-1,3,3a,6,7,7a,8,9,10,11,11a,11b-dodecahydro-8,8,11a-trimethyl-2H-cyclobuta-phenanthrene-3β-carboxylate 
• 152715-35-0 (4aS,4bR,7R,7aR,9aS,10R,11aS)-10-Butyryloxy-1,1,4a-trimethyl-1,3,4,4a,4b,5,6,7,7a,10,11,11a-dodecahydro-2H-cyclobuta[j]phenanthrene-7-carboxylic acid 

Relevant academic research and scientific papers

Spongian Pentacyclic Diterpenes. Stereoselective Synthesis of Aplyroseol-1, Aplyroseol-2 and Deacetylaplyroseol-2

Natural spongian pentacyclic diterpenes aplyroseol-1 19, aplyroseol-2 18 and deacetylaplyroseol-2 17 have been synthesized in enantiomerically pure form from (+)-podacarp-8(14)-en-13-one 3.Key intermediate in these syntheses is a suitably substituted acid-dialdehyde 2, which is prepared from enone 3 by a sequence of transformations involving stereoselective introduction of a C-7 oxygen functionality, photoaddition of acetylene to the C(8)-C(14) double bond to form a cyclobutene ring system, reductive cyanation of the C-13 carbonyl group, hydrolysis of the resulting nitrile group, and ozonolysis of the cyclobutene moiety.An intramolecular participation of the 7α-hydroxy group in the hydrolysis of the 13α-nitrile 8 is set in focus.