468-76-8

Basic information

• Product Name: cassaine
• Synonyms: cassaine;(Dodecahydro-7.beta.-hydroxy-1.alpha.,4B.beta.,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene)acetic acid 2-(dimethylamino)ethyl ester sulfate;Acetic acid, [(1R,4as,4br,7S,8ar,10as)-dodecahydro-7-hydroxy-1,4B,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]-, 2-(dimethylamino)ethyl ester, (2E)-;Aids002656;Aids-002656;Diterpene alkaloid;Nsc72302;Podocarpane-D13,A-acetic acid, 3B-hydroxy-14A-methyl-7-oxo-, 2-(dimethylamino)ethyl ester, (E)-
• CAS NO: 468-76-8
• Molecular Formula: C24H39NO4
• Molecular Weight: 405.575
• Mol File: 468-76-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 142.5°
• Boiling Point: 517.9°Cat760mmHg
• Flash Point: 267°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 6.87E-13mmHg at 25°C
• Refractive Index: 1.537
• PKA: 15.04±0.70(Predicted)
• CAS DataBase Reference: cassaine(CAS DataBase Reference)
• NIST Chemistry Reference: cassaine(468-76-8)
• EPA Substance Registry System: cassaine(468-76-8)

Safety Data

• Hazardous Substances Data: 468-76-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C24H39NO4/c1-15-16(13-21(28)29-12-11-25(5)6)7-8-17-22(15)18(26)14-19-23(2,3)20(27)9-10-24(17,19)4/h13,15,17,19-20,22,27H,7-12,14H2,1-6H3/b16-13+/t15-,17-,19-,20-,22-,24+/m0/s1

Upstream product

• 1492141-97-5 (2S,4aS,7S,8aR)-2-(benzyloxy)-1,1,4a-trimethyl-7-(prop-1-en-2-yl)decahydronaphthalene 
• 1569079-85-1 C₂₃H₃₆O₃ 
• 1492141-98-6 1-((2S,4aS,7S,8aR)-7-(benzyloxy)-4a,8,8-trimethyldecahydronaphthalen-2-yl)ethanone 
• 1492141-99-7 (2S,4aS,7S,8aR)-7-(benzyloxy)-4a,8,8-trimethyldecahydronaphthalen-2-yl acetate 
• 1492142-00-3 (2S,4aS,7S,8aR)-7-(benzyloxy)-4a,8,8-trimethyldecahydronaphthalen-2-ol 
• 1492142-01-4 (4aR,7S,8aR)-7-(benzyloxy)-4a,8,8-trimethyloctahydronaphthalen-2(1H)-one 
• 1492142-02-5 (4aR,6S,8aR)-methyl 6-(benzyloxy)-5,5,8a-trimethyl-3-oxodecahydronaphthalene-2-carboxylate 
• 1492142-03-6 (4aR,6S,8aR)-methyl 6-(benzyloxy)-5,5,8a-trimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 1492142-04-7 (2S,4aS,8S,8aR,10aR)-methyl 2-(benzyloxy)-1,1,4a,8-tetramethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carboxylate 
• 1492142-05-8 (1S,4bS,7S,8aR)-7-(benzyloxy)-1,4b,8,8-tetramethyl-1,2,5,6,7,8,8a,9-octahydrophenanthrene-3,10(4H,4bH)-dione 
• 1492142-06-9 (2S,4aS,6R,8S,10aR)-2-(benzyloxy)-6-hydroxy-1,1,4a,8-tetramethyl-2,3,4,4a,5,6,7,8,10,10a-decahydrophenanthren-9(1H)-one 
• 1492142-07-0 (2S,4aS,6R,8S,10aR)-2-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-1,1,4a,8-tetramethyl-2,3,4,4a,5,6,7,8,10,10a-decahydrophenanthren-9(1H)-one 
• 1492142-08-1 (2S,4aS,6R,8S,10aR)-6-((tert-butyldimethylsilyl)oxy)-2-hydroxy-1,1,4a,8-tetramethyl-2,3,4,4a,5,6,7,8,10,10a-decahydrophenanthren-9(1H)-one 

Downstream Products

• 57289-50-6 (3β-hydroxy-7-oxo-14α-methyl-podocarpanyl-(13α))-acetic acid 
• 468-74-6 Cassainsaeure 

Relevant articles and documents

Anionic polycyclization entry to tricycles related to quassinoids and terpenoids: A stereocontrolled total synthesis of (+)-cassaine

A full account of our anionic polycyclization approach to access highly functionalized tricycles related to quassinoids and terpenoids from several optically active bicyclic enone systems and Nazarov reagents is presented. (+)-Carvone is the only chiral s

Total synthesis of (+)-cassaine via transannular diels-alder reaction

A full account of the total synthesis of (+)-cassaine (1) using the transannular Diels-Alder (TADA) reaction as the pivotal construction is described. The strategy began from Evans' oxazolidine 8, the only chiral source used for the total stereochemical outcome of the target molecule. The key intermediate 3 was obtained from 8 in 10 steps in 40% overall yield. Following extensive optimization, the coupling of 3 on both ends with another densely functional partner 2 followed by TADA reaction on macrocycle 4 cleanly furnished the tricycle 5. The stereochemical outcome in 5 was expected via a least-energetic transition state T4. A stereoselective reduction, hydroboration, and methyl cuprate 1,4-addition along with a few other functional interconversions transformed 5 into the key intermediate 37. Final tethering of dimethylaminoethyloxycarbonyl along with epimerization at C8 and alcohol deprotection at C3 yielded the natural product 1.