90122-78-4

Upstream product

• 89295-88-5 (+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-2-(bisdimethylaminophosphoryloxy)-1,5α,6α,8aβ-tetramethyl-5β-vinylnaphthalene 
• 90122-75-1 C₂₀H₃₉N₂O₃P 
• 10463-42-0 3,4-dimethyl-cyclohex-2-enone 
• 89295-86-3 (+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-1β-hydroxymethyl-5α,6α,8aβ-trimethyl-5β-vinyl-2(1H)-naphthalenone 
• 122058-21-3 Methanesulfonic acid (1S,4aS,5S,6R,8aS)-5,6,8a-trimethyl-2-oxo-5-vinyl-decahydro-naphthalen-1-ylmethyl ester 
• 89295-87-4 (+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-5α,6α,8aβ-trimethyl-1-methylene-5β-vinyl-2(1H)-naphthalenone 
• 69748-95-4 (+/-)-4,4aβ,5,6,7,8-hexahydro-5α,6α-dimethyl-5β-vinyl-2(3H)-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.