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Synfacts 2019; 15(06): 0589
DOI: 10.1055/s-0037-1611622
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Endiandric Acids

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Nicolaou KC. * Petasis NA, Zipkin RE, Uenishi J. University of Pennsylvania, Philadelphia, USA
The Endiandric Acid Cascade. Electrocyclizations in Organic Synthesis. 1. Stepwise, Stereocontrolled Total Synthesis of Endiandric Acids A and B.

J. Am. Chem. Soc. 1982;
104: 5555-5557
CrossrefGoogle Scholar
Nicolaou KC. * Petasis NA, Uenishi J, Zipkin RE.
The Endiandric Acid Cascade. Electrocyclizations in Organic Synthesis. 2. Stepwise, Stereocontrolled Total Synthesis of Endiandric Acids C–G.

J. Am. Chem. Soc. 1982;
104: 5557-5558
CrossrefGoogle Scholar
Nicolaou KC. * Zipkin RE, Petasis NA.
The Endiandric Acid Cascade. Electrocyclizations in Organic Synthesis. 3. "Biomimetic" Approach to Endiandric Acids A-G. Synthesis of Precursors.

J. Am. Chem. Soc. 1982;
104: 5558-5560
CrossrefGoogle Scholar
Nicolaou KC. * Petasis NA, Zipkin RE.
The Endiandric Acid Cascade. Electrocyclizations in Organic Synthesis. 4. Biomimetic Approach to Endiandric Acids A-G. Total Synthesis and Thermal Studies.

J. Am. Chem. Soc. 1982;
104: 5560-5562
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
20 May 2019 (online)

 
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Key words

endiandric acids - electrocyclization - Glaser coupling - Diels–Alder reaction - biomimetic synthesis

Significance

Nicolaou and co-workers describe the total synthesis of the endiandric acids. Their approach exploits a cascade of pericyclic reactions, which allow assembly of the carbon skeletons in one step. This pathway had been hypothesized to be the biosynthetic origin of these natural products.


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Comment

Aldehyde C was chosen as a common intermediate for the synthesis of alkynes E and G. Glaser coupling, oxidation, and elimination results in the formation of dialkyne H. Partial reduction to polyolefin I results in a series of electrocyclizations and cycloadditions giving rise to the target structures.


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