40184-98-3

Usage

InChI:InChI=1/C25H38O2/c1-14(2)16-7-9-23(4)13-20-17(12-19(16)23)21(22(26)27)25-11-6-15(3)18(25)8-10-24(20,25)5/h14-16,18-20H,6-13H2,1-5H3,(H,26,27)/t15-,16+,18+,19+,20+,23-,24+,25?/m1/s1

Upstream product

• 119988-00-0 (1aR,3aS,4R)-1-((3S,3aS,7aR)-3-Isopropyl-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl)-1a,4-dimethyl-2-oxo-octahydro-cyclopropa[c]pentalene-1-carboxylic acid ethyl ester 
• 119987-99-4 Ethyl <3R-(3α,3aα,5aβ,5bβ,6aβ,9α,9aα,11aS^*)>-5-oxo-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-3,5a,6a-trimethyl-9-isopropyl-1H-pentaleno<1,6a-a>-s-indacene-11-carboxylate 
• 119987-99-4 Ethyl <3R-(3α,3aα,5aβ,5bα,6aβ,9α,9aα,11aS^*)>-5-Oxo-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-3,5a,6a-trimethyl-9-isopropyl-1H-pentaleno<1,6a-a>-s-indacene-11-carboxylate 
• 122047-71-6 (3R,3aS,5aS,5bS,6aR,9S,9aS)-5-Hydroxy-9-isopropyl-3,5a,6a-trimethyl-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-1H-pentaleno[1,6a-a]-s-indacene-11-carboxylic acid ethyl ester 
• 122047-71-6 (3R,3aS,5aS,5bR,6aR,9S,9aS)-5-Hydroxy-9-isopropyl-3,5a,6a-trimethyl-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-1H-pentaleno[1,6a-a]-s-indacene-11-carboxylic acid ethyl ester 
• 119987-98-3 Ethyl <3R-(3α,3aα,5aβ,5bα,6aβ,9α,9aα,11aS^*)>-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-3,5a,6a-trimethyl-9-isopropyl-1H-pentaleno<1,6a-a>-s-indacene-11-carboxylate 
• 119987-98-3 Ethyl <3R-(3α,3aα,5aβ,5bβ,6aβ,9α,9aα,11aS^*)>-2,3,3a,4,5,5a,5b,6,6a,7,8,9,9a,10-tetradecahydro-3,5a,6a-trimethyl-9-isopropyl-1H-pentaleno<1,6a-a>-s-indacene-11-carboxylate 

Relevant academic research and scientific papers

and Annulation of Enones. Enantiocontrolled Total Synthesis of (-)-Retigeranic Acid

The lithium dienolates of ethyl 2-bromocrotonate and of other, more highly substituted α-bromocrotonates underwent smooth addition to enones to provide, in one step, the corresponding vinylcyclopropanes in excellent yields.The vinylcyclopropanes were subjected to several modes of rearrangement: thermolysis to afford annulated cyclopentenes in an overall annulation sequence; conversion to enol ethers to give, via the Cope rearrangement of divinylcyclopropanes, bicyclo systems; and nucleophilic opening with trimethylsilyl iodide to afford, at lowtemperatures, intermediate allylic iodides that were cyclized to annulated cyclopentenes under basic conditions.The stereochemical details of the vinylcyclopropanation and the cyclopentene rearrangement were investigated.The application of this process was realized by the convergent and enantiocontrolled total synthesis of (-)-retigeranic acid.The scope, the limitation, and some future applications of this methodology are indicated.

SHORT, ENANTIOSELECTIVE SYNTHESIS OF (-)-RETIGERANIC ACID VIA ANNULATION.

The total synthesis of retigeranic acid 1 was achieved in 14 steps from menthene.The key features involved the vinylcyclopropanation of enone 6 with the dienolate anion of 5 to furnish vinylcyclopropane 4 and its rearrangement to pentacycle 3 in an overall cyclopentene annulation sequence.