Enantioselective Total Syntheses of (+)- and (-)-Ottelione A and (+)- and (-)-Ottelione B. Absolute Configuration of the Novel, Biologically Active Natural Products.

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

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Enantioselective constructions of quaternary carbons and their application to the asymmetric total syntheses of fredericamycin A and discorhabdin A

Pure and Applied Chemistry ◽

10.1351/pac200779040701 ◽

2007 ◽

Vol 79 (4) ◽

pp. 701-713 ◽

Cited By ~ 22

Author(s):

Yasuyuki Kita ◽

Hiromichi Fujioka

Keyword(s):

Natural Products ◽

Optically Active ◽

Biologically Active ◽

Hypervalent Iodine ◽

Total Syntheses ◽

Carbon Centers ◽

Phenol Derivatives ◽

Fredericamycin A ◽

Active Natural ◽

Quaternary Carbons

An efficient enantioselective construction of quaternary carbons including spiro carbons is an area of intense interest due to the importance of these units as components of biologically active natural products. Prominent methods are presented for the synthesis of chiral, nonracemic quaternary carbon centers by (i) stereospecific rearrangement of optically active epoxides, (ii) enzyme-catalyzed resolution, and (iii) hypervalent iodine reagent-induced ipso-substitution of para-substituted phenol derivatives. These methods were applied to the total syntheses of fredericamycin A and discorhabdin A.

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ChemInform Abstract: Total Syntheses of Biologically Active Natural Products by Claisen Rearrangement of Simple Chiral Templates

ChemInform ◽

10.1002/chin.199019335 ◽

1990 ◽

Vol 21 (19) ◽

Author(s):

T. SUZUKI ◽

E. SATO ◽

K. UNNO

Keyword(s):

Natural Products ◽

Claisen Rearrangement ◽

Biologically Active ◽

Total Syntheses ◽

Active Natural

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Assignment of the absolute configuration of large molecules by ab initio calculation of the rotatory power within a small basis set scheme: the case of some biologically active natural products

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2004.05.023 ◽

2004 ◽

Vol 15 (13) ◽

pp. 1979-1986 ◽

Cited By ~ 9

Author(s):

Egidio Giorgio ◽

Rosario G Viglione ◽

Carlo Rosini

Keyword(s):

Natural Products ◽

Ab Initio ◽

Absolute Configuration ◽

Ab Initio Calculation ◽

Rotatory Power ◽

Biologically Active ◽

Basis Set ◽

Large Molecules ◽

The Absolute ◽

Active Natural

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Approaches to the stereoselective total synthesis of biologically active natural products

Pure and Applied Chemistry ◽

10.1351/pac200577010103 ◽

2005 ◽

Vol 77 (1) ◽

pp. 103-117 ◽

Cited By ~ 5

Author(s):

Anne Baron ◽

Matthew Ball ◽

Benjamin Bradshaw ◽

Sam Donnelly ◽

Olivier Germay ◽

...

Keyword(s):

Natural Products ◽

Double Bond ◽

Total Synthesis ◽

Recent Work ◽

Biologically Active ◽

Total Syntheses ◽

Trisubstituted Double Bond ◽

Epothilone B ◽

Active Natural

Total syntheses of epothilone B and pamamycin 607, which feature reactions between functionalized allylstannanes and aldehydes to introduce a (Z)-trisubstituted double-bond and remote stereocenters stereoselectively, are discussed. Recent work concerned with carrying out this chemistry without the use of allylstannanes as starting materials and progress toward a total synthesis of bryostatins are also presented.

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