80287-17-8

Basic information

• Product Name: 16(R),19(Z)-isositsirikine
• CAS NO: 80287-17-8
• Molecular Weight: 354.449
• Mol File: 80287-17-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 16(R),19(Z)-isositsirikine(CAS DataBase Reference)
• NIST Chemistry Reference: 16(R),19(Z)-isositsirikine(80287-17-8)
• EPA Substance Registry System: 16(R),19(Z)-isositsirikine(80287-17-8)

Safety Data

• Hazardous Substances Data: 80287-17-8(Hazardous Substances Data)

Upstream product

• 73385-57-6 4,21-dehydrogeissoschizine hydrochloride 
• 6519-40-0 16R-19,20-E-Isositsirikine acetate 
• 32789-73-4 20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine 
• 439-66-7 (Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate 
• 19456-89-4 strictosidine 
• 118577-70-1 (+/-)-3-isogeissoschizine 
• 23107-03-1 methyl 2-((12b,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate 
• 114252-07-2 (E)-3-((2S,12bS)-2-Ethoxycarbonylmethyl-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-3-yl)-acrylic acid methyl ester 
• 118577-67-6 (E)-3-((2S,12bS)-2-Ethoxycarbonylmethyl-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-3-yl)-acrylic acid ethyl ester 
• 102976-89-6 (E)-3-[(2R,12bS)-2-(Ethoxycarbonyl-methylsulfanyl-methyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-3-yl]-acrylic acid methyl ester 
• 118577-66-5 (E)-3-[(2R,12bS)-2-(Ethoxycarbonyl-methylsulfanyl-methyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-3-yl]-acrylic acid ethyl ester 
• 67685-79-4 2-[(2S,12bS)-3-((E)-2-Methoxycarbonyl-vinyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-2-yl]-malonic acid dimethyl ester 
• 23107-03-1 (+/-)-(19Z)-Methyl Geissoschizoate 
• 61-54-1 tryptamine 

Relevant articles and documents

A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate

Monoterpene indole alkaloids comprise a diverse family of over 2000 plant-produced natural products. This pathway provides an outstanding example of how nature creates chemical diversity from a single precursor, in this case from the intermediate strictosidine. The enzymes that elicit these seemingly disparate products from strictosidine have hitherto been elusive. Here we show that the concerted action of two enzymes commonly involved in natural product metabolism - A n alcohol dehydrogenase and a cytochrome P450 - produces unexpected rearrangements in strictosidine when assayed simultaneously. The tetrahydro-β-carboline of strictosidine aglycone is converted into akuammicine, a Strychnos alkaloid, an elusive biosynthetic transformation that has been investigated for decades. Importantly, akuammicine arises from deformylation of preakuammicine, which is the central biosynthetic precursor for the anti-cancer agents vinblastine and vincristine, as well as other biologically active compounds. This discovery of how these enzymes can function in combination opens a gateway into a rich family of natural products.

ALKALOIDS FROM RHAZYA STRICTA

Chemical investigations of roots and leaves of Rhazya stricta have resulted in the isolation of the new indole alkaloids, 16R-19,20-E-isositsirikine acetate, leepacine and dihydroeburnamenine, along with six known alkaloids.Among these, (-)-16R,21R-O-methyleburnamine, 2-ethyl-3-indole, (20S)-19,20-dihydrocondylocarpine and N-acetylaspidospermidine have been isolated for the first time from R. stricta.Spectral studies on (+)-21S-eburnamenine and the glycoalkaloid strictosamide have also been undertaken. --- Key Word Index: Rhazya stricta; Apocynaceae; indole alkaloide; glycoalkaloids; 13C NMR.

Preparation and H(3) Isomerization of C(15)-Substituted Deplancheine Derivatives. Synthesis of Geissoschizol and Geissoschizine

A series of indoloquinolizidines have been prepared by the two-step scheme of nucleophile addition to 1-tryptophyl-3-acylpyridinium salts or their vinylogues and subsequent, acid-catalyzed cyclization.Acid-induced hydrolysis, decarboxylation, and reduction of the resultant vinylogous urethanes has opened an approach to antirhine and yielded C(15)-substituted deplancheine derivatives.Functional group manipulation of the latter has permitted the syntheses of geissoschizol and geissoschizine.