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Porantherine

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Porantherine
Category Others
Catalog number BBF-05254
CAS 33529-61-2
Molecular Weight 217.35
Molecular Formula C15H23N
Purity ≥95% by HPLC

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is a polycyclic alkaloid obtained from the shrub Poranthera corymbosa.

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Related CAS 108818-56-0 (hydrochloride) 54382-19-3 ((±)-form)
Synonyms (1R,6aS)-3aβ,4,5,6,7,8,9,9a-Octahydro-9aβ-methyl-1H-1,6a-ethanopyrido[2,1,6-de]quinolizine; (1S,4R,7S,9R)-9-Methyl-8-azatetracyclo[5.5.3.01,8.04,9]pentadec-5-ene; (1R,3aS,6aS,9aR)-3a,4,5,6,7,8,9,9a-octahydro-9a-methyl-1H-1,6a-ethanopyrido[2,1,6-de]quinolizine
Storage Store at -20°C
IUPAC Name (1R,4R,7S,9S)-9-methyl-8-azatetracyclo[5.5.3.01,8.04,9]pentadec-5-ene
Canonical SMILES CC12CCCC34N1C(CCC3)C=CC2CC4
InChI InChI=1S/C15H23N/c1-14-8-3-10-15-9-2-4-13(16(14)15)6-5-12(14)7-11-15/h5-6,12-13H,2-4,7-11H2,1H3/t12-,13-,14-,15+/m0/s1
InChI Key YXWOUJYNFPKTLH-ZQDZILKHSA-N
Appearance Solid
Boiling Point 309.6±11.0°C at 760 mmHg
Melting Point 36-40°C
Density 1.1±0.1 g/cm3
Solubility Soluble in Chloroform, DMSO, Methanol
1. Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence
Pierre Sancibrao, Delphine Karila, Cyrille Kouklovsky, Guillaume Vincent J Org Chem. 2010 Jun 18;75(12):4333-6. doi: 10.1021/jo100768d.
The application of a sequence involving a nitroso Diels-Alder cycloaddition and a ring-rearrangement metathesis to the total synthesis of (+/-)-8-epihalosaline and the formal synthesis of (+/-)-porantheridine is described. The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot.
2. Stereodivergent synthesis of piperidine alkaloids by ring-rearrangement metathesis/reductive lactam alkylation of nitroso Diels-Alder cycloadducts
Guillaume Vincent, Delphine Karila, Georges Khalil, Pierre Sancibrao, Didier Gori, Cyrille Kouklovsky Chemistry. 2013 Jul 8;19(28):9358-65. doi: 10.1002/chem.201300836. Epub 2013 Jun 5.
A general methodology for the stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids by ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts is reported. The approach is illustrated by the formal synthesis of porantheridine and the total synthesis of andrachcinidine through a diastereodivergent allylation of an N-alkoxy bicyclic lactam. The asymmetric synthesis of the latter alkaloid provides new insights into the configurational stability of cycloadducts between chloronitroso reagents and cyclopentadiene.
3. A formal synthesis of porantheridine and an epimer
Roderick W Bates, Yongna Lu J Org Chem. 2009 Dec 18;74(24):9460-5. doi: 10.1021/jo9021925.
A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.

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