Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-brunsvigine.

  title={Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-brunsvigine.},
  author={Martin Gerhardt Banwell and Okanya J. Kokas and Anthony C. Willis},
  journal={Organic letters},
  volume={9 18},
The readily available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1]. 
40 Citations

Flexible synthesis of montanine-like alkaloids: revisiting the structure of montabuphine.

An efficient and stereocontrolled synthetic strategy towards the synthesis of montanine-like alkaloids was developed. Our results suggest that the structure elucidation for natural montabuphine needs

Synthetic studies on amaryllidaceae and other terrestrially derived alkaloids.

The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these

The role of biocatalysis in the asymmetric synthesis of alkaloids

This article reviews the progress in chemo-enzymatic alkaloid synthesis over the last 25 years, focusing on recent developments that have led to significant improvements in terms of step-economy and

The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin

A seven-step reaction sequence has been used to convert the enantiomerically pure cis-1,2-dihydrocatechol 10 into the cyclohexenone 17a. A near equivalent sequence involving the same starting

Rhodium-Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine-Type Amaryllidaceae Alkaloids.

The present method has been employed to construct synthetically valuable bicyclo[3.3.1]alkenone derivatives and pyrrolidine-ring-containing bicyclic indole compounds and a stereoselective synthesis of 5,11-methanomorphanthridin-3-one, which shares a key skeleton with montanine-type Amaryllidaceae alkaloids has been achieved by using this chemistry.

The Exploitation of Enzymatically-Derived cis-1,2-Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products.

This personal account details the outcomes of a nearly three-decade long campaign within this group to exploit these compounds in the synthesis of a diverse range of small molecule natural product targets.



Mathematical techniques in crystallography and materials science

In the course of 30 years as a practicing crystallographer I have frequently been faced with the necessity of finding out a little bit about some general branch of mathematics with which I was

Details of X-ray analyses carried out as part of this study are provided in the Supporting Information

  • Tetrahedron
  • 1980

maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow

  • Crystallographic Computing
  • 2000

School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, ACT 0200

  • Australia Correspondence e-mail: Received
  • 2007

The Inclusion of Secondary Extinction in Least-Squares Refinement in Crystal Structures

  • 1970

66, 1 and references cited therein

  • 2005


  • Report ORNE-5138. Oak Ridge National
  • 1976