19902-42-2

Upstream product

• 19902-43-3 (+/-)-15,16-epoxy-19-oxo-trans-cleroda-3,13⁽¹⁶⁾,14-triene 
• 30414-53-0 methyl propanoyl acetate 
• 69748-94-3 (+/-)-2-mesyloxymethyl-3α,4α-dimethyl-3β-vinylcyclohexanone 
• 122058-26-8 (1'R,4'aS,5'R,6'S,8'aR)-5'-(2-Furan-3-yl-2-hydroxy-ethyl)-1',5',6'-trimethyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-8'a-carbonitrile 
• 122058-17-7 (1S,2R,4aS,5S,8aR)-1-(2-Furan-3-yl-ethyl)-6-hydroxy-1,2,5-trimethyl-octahydro-naphthalene-4a-carbonitrile 
• 122058-27-9 Acetic acid 2-((1'S,4'aR,5'S,6'R,8'aS)-8'a-cyano-1',5',6'-trimethyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl)-1-furan-3-yl-ethyl ester 
• 122058-16-6 (1'R,4'aS,5'R,6'S,8'aR)-5'-(2-Furan-3-yl-ethyl)-1',5',6'-trimethyl-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-8'a-carbonitrile 
• 89295-95-4 (+/-)-15,16-epoxy-19-nitrilo-trans-cleroda-13⁽¹⁶⁾,14-dien-3-one 
• 89295-96-5 (+/-)-15,16-epoxy-19-nitrilo-trans-cleroda-3,13⁽¹⁶⁾,14-triene 
• 122058-15-5 (+/-)-decahydro-8aα-cyano-2-ethylenedioxy-1α,5α,6α-trimethyl-5β-vinylnaphthalene 
• 89295-94-3 (+/-)-2-(decahydro-8aα-cyano-2-ethylenedioxy-1α,5α,6α-trimethylnaphthalene-5β-yl)acetaldehyde 
• 90122-80-8 (+/-)-(decahydro-8aα-cyano-2-ethylenedioxy-1α,5α,6α-trimethylnaphthalen-5β-yl)-ethanol 
• 89295-93-2 (+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-8aα-cyano-1α,5α,6α-trimethyl-5β-vinyl-2(1H)-naphthalenone 
• 89295-92-1 (+/-)-(4aα,5α,6β)-5-ethenyl-4,4a,5,6,7,8-hexahydro-1,5,6-trimethyl-2(1H)-naphthalenone 

Relevant academic research and scientific papers

A GENERAL METHOD FOR THE SYNTHESIS OF CLERODANE DITERPENOIDS. STEREOSPECIFIC TOTAL SYNTHESES OF (+/-)-15,16-EPOXY-CIS-CLERODA-3,13(16),14-TRIENE AND (+/-)-MAINGAYIC ACID

A general method for the syntheses of cis- and trans-clerodane diterpenoids has been developed and its applications to the total syntheses of both representatives 11 and maingayic acid (32) in racemic forms are described.The common Δ4-3-octalone intermediates 2a and 2b were prepared from 3,4-dimethyl-2-cyclohexenone by a stereospecific conjugate addition-alkylation sequence and the subsequent thermodynamically controlled annelation.The dimethylcuprate addition to 2a followed by enolate trapping afforded stereospecifically the cis-alcohol 12, from which (+/-)-11 has been synthesized.On the other hand hydrocyanation of 2b gave trans-intermediate 33, and then it has been converted to (+/-)-maingayic acid (32).

A Versatile Method for the Synthesis of Clerodane Diterpenoids: Synthesis of cis and trans Representatives

Application of stereospecific conjugate addition reactions to Δ4-3-octalone intermediates has led to the total synthesis of both cis- and trans-clerodane diterpenes.