72629-69-7

Usage

InChI:InChI=1/C20H32O/c1-15(2)19-13-12-17(4)10-6-8-16(3)9-7-11-18(5)14-20(19)21/h8,11-13,15,20-21H,6-7,9-10,14H2,1-5H3/b16-8+,17-12+,18-11+,19-13-/t20-/m0/s1

Upstream product

• 130675-18-2 (2Z,4E,8E)-2-Isopropyl-5,9,13-trimethyl-tetradeca-2,4,8,12-tetraenenitrile 
• 135896-27-4 (2Z,4E)-5,9-dimethyl-2-(1-methylethyl)deca-2,4,8-trienenitrile 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 60755-26-2 2-(Diethylphosphono)-3-methylbutyronitrile 
• 2442-13-9 3,3-dimethoxy-2-methyl-butan-2-ol 
• 130675-18-2 (2Z,4E,8E,12E)-2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile 
• 135896-18-3 (2Z,4E,8E,12E)-14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraene-1-ol 
• 123979-87-3 Ethyl (2Z,4E,8E,12E)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate 
• 123979-88-4 Ethyl (2Z,4E,8E,12E)-14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate 
• 148515-21-3 ethyl 2-(diethoxyphosphoryl)-3-methylbutyrate 
• 502-67-0 Farnesal 
• 88924-81-6 (1Z,3E,7E,11S,12S,14S)-11,12-epoxy cembra-1,3,7-trien-14-ol 
• 153744-68-4 (5E,9E,11Z)-(R)-2-Isopropenyl-12-isopropyl-5,9-dimethyl-oxacyclotrideca-5,9,11-triene 
• 77394-15-1 (2Z,4E,8E,12E)-2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one 

Relevant academic research and scientific papers

Stereo- and enantioselective total synthesis of sarcophytol-A

The first total synthesis of sarcophytol-A, a biologically important marine cembranoid, was achieved in a highly stereo- and enantioselective manner.

A ketal Claisen rearrangement for α-ketol isoprene unit elongation: application to a practical synthesis of sarcophytol A intermediate

A new ketal Claisen rearrangement using the ketal 10 for the isoprene unit elongation which affords terminal α-ketol terpenoid is presented.Its efficiency is demonstrated by successful transformation of the product of this reaction, the α-ketol 20, into 2, the acyclic precursor of sarcophytol A total synthesis, by two alternative routes via the β,γ-unsaturated aldehyde 24 and the allylic alcohol 28.

Total Synthesis of Sarcophytol A, an Anticarcinogenic Marine Cembranoid

A highly stereo- and enantioselective total synthesis of sarcophytol A (1), a marine cembranoid promising as a cancer chemopreventive agent, is described.The nitrile 10 obtained Z-selectively (Z:E = >35:1) by the Horner-Emmons reaction of (E,E)-farnesal (5) with the phosphononitrile 9 in 91percent yield was converted to the conjugated 2(Z),4(E)-dienal 3 in which the terminal (E)-methyl group was functionalized.Intramolecular alkylation of the cyanohydrin TMS ether of 3 provided the macrocyclic ketone 2 in 79percent of overall yield from 3 without isolation of the cyclic cyanohydrin 20 as well as its TMS ether 19.Reduction of 2 with several chiral LiAlH4 reagents afforded 1 highly enantioselectively (87-93percent ee) in 78-97percent yield from which enantiomerically pure 1 (>99percent ee) was readily obtained upon a single recrystallization.

Total Syntheses of Both Enantiomers of Sarcophytols A and T Based on Stereospecific Wittig Rearrangement

Both enantiomers of sarcophytols A (1) and T (2), cembranolide diterpenes isolated from a soft coral, were syntesized from a common chiral intermediate, obtained by baker's yeast reduction, using a stereospecific Wittig rearrangement as the key step.

Studies of Australian Soft Corals. XXXIII. New Cembranoid Diterpenes from a Lobophytum Species

The isolation of two new cembranoid diterpenes, (14S,1E,3E,7E)-14-acetoxy-11,12-epoxycembra-1,3,7-triene and the corresponding 14-alcohol, is reported from the soft coral Lobophytum sp.A minor component in the extract (3S,4S,11S,12S,1E,7E)-3,4:11,12-bisepoxycembra-1,7-diene was identified but may be artefactual as it is the sole product of the aerial oxidation of the major metabolite (11S,12S,1E,3E,7E)-11,12-epoxycembra-1,3,7-triene.Further examples of stereospecific epoxidations are reported.