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R: Total synthesis of Minfiensine - 864.5 kb

Q : Total synthesis of Tangutorine - 395.2 kb

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R : Total synthesis of Tangutorine - 445.5 kb

Tital: Total Synthesis of Minfiensine,Vincorine and Harringtonolide

Speaker: Dr. Min Zhang, research fellow of Innovative Drug Research Centre(IDRC), ChongQing University, China

Total synthesis of Englerin A - 342.8 kb

17. Huang, J.; Foyle, D.; Lin, X.; Yang, J. "Total synthesis and biological evaluation of an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid" J. Org. Chem. 2013, 78, 9166-9173.

R : Total synthesis of E­nglerin A - 533.2 kb

Q: Total Synthesis of (±)-Maoecrystal V - 354.4 kb

12. Yang, J.; Xue, H. “Transannular Reactions in Total Synthesis” in Stereoselective Synthesis of Drugs and Natural Products Andrushko, V and Andrushko, N. Editors; Wiley-Blackwell, John Wiley & Sons Inc., 2013, Chapter 20.

This paper summarizes the progress on the total syntheses of natural products accomplished in mainland China during the period from 2006 to 2010. The overview focuses on the first total synthesis of natural products of contemporary interest including alkaloids, cyclopeptides and cyclic depsipeptides, macrolides, terpenoids and steroids, saponins and glycosides. The development of novel synthetic strategies and methodologies, and application of new selective synthetic methods in the total syntheses of natural products are included as well.

R: Total Synthesis of (±)-Maoecrystal V. - 159.8 kb

Q : Total Synthesis of (-)Morphine - 362.5 kb

13. Huang, J.; Yang, J. R.; Zhang, J.; Yang, J. "Total synthesis and structure-activity relationship sturdy of the potent cAMP signaling agonist (-)-alotaketal A" Org. Biomol. Chem. 2013, 11, 3212-3222.

8. Huang, J.; Yang, J. R.; Zhang, J.*; Yang, J.* "Total synthesis of the potent cAMP signaling agonist (-)-alotaketal A" J. Am. Chem. Soc. 2012, 134, 8806-8809.

For a discussion of the problem of total synthesis within the context of a specific natural product/medicinal agent, see: A.
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  • Nine-Step Enantioselective Total Synthesis of (−)-Vincorine

    Total Synthesis of Akuammiline Alkaloid (−)-Vincorine via Intramolecular Oxidative Coupling

  • Total Synthesis of (±)-Corymine | Read by QxMD

    This work was carried out as part of our efforts toward total synthesis of vincorine and similar alkaloids

  • A recent synthesis of vincorine, ..

    The group publishes a nine-step enantioselective synthesis of vincorine

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Total Synthesis of Minfiensine by MacMillan

Having achieved the total synthesis of (+)-scholarisine A (1), we turned our attention to devising a substrate that would hold the promise of providing access to other members of the akuammiline alkaloid family via a late stage “retrobiosynthetic” strategy. We focused on utilizing synthetic (+)-scholarisine A (1) to access aldehyde 79 (), a carboxylate congener of aldehyde 2 ().

Total Synthesis of Minfiensine ..

The first total synthesis of (+)-scholarisine A (1) has been achieved, employing a longest linear reaction sequence of 25 steps from commercially available anhydride 35. Key synthetic tactics include a novel cyclization, comprising nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer synthetic protocol; an oxidative-lactonization of a diol in the presence of an indole ring; and a late stage cyclization to complete the caged ring scaffold of (+)-scholarisine A (1). A “retrobiosynthetic” fragmentation of totally synthetic (+)-scholarisine A (1) has also been achieved. Studies are currently underway to exploit this fragmentation to gain access to related members of the akuammiline family.

Asymmetric Total Synthesis of Alkaloids 223A and 6 …

In summary, the total synthesis of (+)-minfiensine (1) was completed in nine steps and 21% overall yield from commercial materials. Prominent features of this synthesis include (i) a new cascade organocatalysis sequence to build the central tetracyclic pyrroloindoline framework and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system.

Total Synthesis and Reassignment of (-)-Fusarisetin A ..

The discovery that diol (+)-62 could be obtained in good yield with the appropriate stereogenicity led rapidly to a path forward, as outlined in retrospective fashion in . Indole (−)-52 would first be converted to diol (+)-62 as described above. Oxidative lactonization would then be performed, followed by protecting group exchange, to yield indole alcohol 64 (). Activation of the hydroxyl group would permit cyclization to form the indolenine quaternary center. Deprotection followed by amine oxidation would then complete the total synthesis of (+)-scholarisine A (1).

Total Synthesis of (-)-Vincorine

Over the last 50 years, the Strychnos alkaloids have become recognized as a family of molecular benchmarks, used to calibrate the utility of new complexity-generating reactions or novel synthetic strategies. In this context, minfiensine (1), a structurally unique isolation product from Strychnos minfiensis, has received considerable attention from the chemical synthesis community, culminating recently in the highly elegant (and first) enantioselective total synthesis by Overman and coworkers. Minfiensine is characterized by an embedded 1,2,3,4-tetrahydro-9a,4a-(iminoethano)-9H-carbazole moiety, a tetracyclic core that is also found among related akuammiline alkaloids vincorine (2) and echitamine (3). In this communication, we document a new organocatalytic Diels–Alder/amine cyclization sequence that allows rapid and enantioselective access to this tetracyclic carbazole framework using only an amine catalyst, propynal, and a simple tryptamine derivative. Moreover, we elaborate upon this new asymmetric protocol to achieve a nine-step total synthesis of minfiensine beginning from commercial materials.

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